Biofouling resistant coatings and methods of making and using the same

ABSTRACT

Disclosed herein are compositions to use in biofouling-resistant coatings, biofouling-resistant coatings, methods of making biofouling-resistant coatings, biofouling-resistant devices, and methods of making biofouling-resistant devices.

CROSS-REFERENCE

This application claims benefit of U.S. Provisional Patent ApplicationNo. 62/857,725, filed on Jun. 5, 2019, the contents of which are fullyincorporated by reference herein.

BACKGROUND

Hospital acquired infections (HAIs) cause over 100,000 deaths per yearand over $30 billion in direct healthcare cost. In some cases, medicaldevices implanted into the body are the source of the HAI. Planktonicbacteria adhere to the surface of the medical devices and begin to growinto resilient biofilms that become more resistant to antibiotics anddisinfecting agents than in the planktonic state.

SUMMARY

Described herein, in certain embodiments, are compositions to use inbiofouling-resistant coatings, biofouling-resistant coatings, methods ofmaking biofouling-resistant coatings, biofouling-resistant devices, andmethods of making biofouling-resistant devices.

In one aspect, described herein is a compound of Formula (I):

-   -   wherein    -   A is selected from —C(═O)—, —S(═O)—, —S(═O)₂—, and        —S(═O)(—NR³)—;    -   L is selected from —OQ, —NR³Q, and —N(R³)₂Q⁺;    -   Q is a structure represented by a formula:

-   -   Z is selected from —CR^(6a)R^(6b)—, —C(═O)—, —C(═NH)—, and        —C(═NH)NR⁷—;    -   m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each R³ is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄ alkyl,        optionally substituted aryl, and —X-optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(4a), R^(4b), R^(5a), R^(5c), R^(6a), and R^(6b) is        independently selected from hydrogen, halogen, —CN, —OH,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted aryl, —NR^(8a)R^(8b),        —NR^(8a)R^(8b)R^(8c), —S(═O)₂O⁻, —S(═O)₂OR⁹, —C(═O)O⁻, and        —C(═O)OR⁹;    -   R^(5b) is —OR^(10b), —NR^(10a)R^(10b), or        —NR^(10a)R^(10b)R^(10c+);    -   each R⁷, R^(8a), R^(8b), R^(8c), and R⁹ is independently        selected from hydrogen and optionally substituted C₁-C₄ alkyl,        and optionally substituted aryl;    -   each R^(10a) and R^(10c) is independently selected from        hydrogen, optionally substituted C₁-C₄ alkyl, optionally        substituted aryl, -(optionally substituted        C₁-C₈alkylene)S(═O)₂O⁻, -(optionally substituted        C₁-C₈alkylene)S(═O)₂OH, -(optionally substituted        C₁-C₈alkylene)C(═O)O⁻, and -(optionally substituted        C₁-C₈alkylene)C(═O)OH; and    -   R^(10b) is —C(═O)—C₂-C₆alkenyl, —S(═O)—C₂-C₆alkenyl, or        —S(═O)₂—C₂-C₆alkenyl;    -   provided that a compound of Formula (I) is not        N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide;    -   N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide; or    -   2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

In another aspect, described herein is a compound of Formula (II):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OH,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   x is 0.001-0.999; and    -   wherein the compound of Formula (II) is charged or zwitterionic;    -   provided that a compound of Formula (II) is not

In another aspect, described herein is a compound of Formula (III):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a);    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   x is 0.001-0.999.

In another aspect, described herein is a copolymer comprising:

a) a repeating unit of Formula (VII):

wherein,

-   each R^(1a) and R^(1b) is independently selected from hydrogen and    halogen;-   each R^(2a) and R^(2b) is independently selected from halogen, —CN,    and optionally substituted C₁-C₆ fluoroalkyl;-   each A¹ and A² is independently selected from —C(═O)—, —S(═O)—,    —S(═O)₂—, and —S(═O)(═NR^(3c))—;-   each B¹ and B² is independently selected from —O— and —NR^(3c)—;-   Z¹ is —(CR^(6c)R^(6d))_(s)—;-   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is    independently selected from hydrogen, halogen, —CN, —OR^(9a),    optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄    fluoroalkyl, optionally substituted C₂-C₆ alkenyl, —NR^(3c)R^(3d),    —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(11a), R^(11b), and R^(11c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and-   s is an integer selected from 1, 2, 3, 4, and 5;    b) a repeating unit of Formula (VIII):

wherein,

-   A³ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B³ is —O— or —NR^(3c)—;-   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);-   Z² is —(CR^(6c)R^(6d))_(t)—;    Z³ is —(CR^(6c)R^(6d))_(p)—;-   each R^(3a) and R^(3b) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, and optionally substituted    benzyl;    each R^(6c) and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(12a), R^(12b), and R^(12c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   t is an integer selected from 1, 2, 3, 4, or 5;-   p is an integer selected from 1, 2, 3, 4, or 5; and-   wherein the repeating unit of Formula (VIII) is charged or    zwitterionic; and    c) a repeating unit of Formula (IX):

wherein,

-   A⁴ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B⁴ is —O— or —NR^(3c)—;-   Z⁴ is —(CR^(6c)R^(6d))_(k)—;-   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+),    optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆    fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);-   each R^(6c), and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(9b), R^(9c), R^(13a), R^(13b), and R^(13c) is    independently selected from hydrogen, optionally substituted C₁-C₄    alkyl, and optionally substituted aryl; and-   k is an integer selected from 1, 2, 3, 4, or 5.

Any combination of the groups described above or below for the variousvariables is contemplated herein. Throughout the specification, groupsand substituents thereof are chosen by one skilled in the field toprovide stable moieties and compounds.

In another aspect, described herein is a medical device coated with acompound of Formula (I), (II), or (III).

In another aspect, described herein is a medical device coated with acopolymer comprising a repeating unit of Formula (VII), (VIII), and(IX).

In another aspect, described herein is a biofouling-resistant medicaldevice, wherein a surface of the medical device is coated with a phenylazide-based copolymer having a number-average molecular weight ofbetween about 10,000 and about 250,000.

In another aspect, described herein is a biofouling-resistant medicaldevice, wherein a surface of the medical device is coated with a phenylazide-based copolymer having a number-average molecular weight ofbetween about 14,000 and about 21,000.

In another aspect, described herein is a biofouling-resistant medicaldevice, wherein a surface of the medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of betweenabout 1 and 1.5.

In another aspect, described herein is a method of preparing abiofouling-resistant medical device, comprising:

-   -   a) contacting a surface of a medical device with a mixture        comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the medical device of step a) with a        light source for a time sufficient to undergo photografting of        the charged or zwitterion copolymer onto the surface of the        medical device, thereby making the biofouling-resistant medical        device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        10,000 and about 250,000.

In another aspect, described herein is a method of preparing abiofouling-resistant medical device, comprising:

-   -   a) contacting a surface of a medical device with a mixture        (e.g., a solution) comprising a charged or zwitterion copolymer;        and    -   b) treating the surface of the medical device of step a) with a        light source for a time sufficient to undergo photografting of        the charged or zwitterion copolymer onto the surface of the        medical device, thereby making the biofouling-resistant medical        device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        14,000 and about 21,000.

In another aspect, described herein is a method of preparing a chargedor zwitterion copolymer modified biofouling-resistant device comprising:

-   -   a) contacting a surface of a silicon-based device with a mixture        (e.g., a solution) comprising a charged or zwitterion copolymer;        and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the        silicon-based device, thereby generating the charged or        zwitterion copolymer modified device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer.

In another aspect, described herein is a method of preparing a chargedor zwitterion copolymer modified biofouling-resistant device comprising:

-   -   a) contacting a surface of a device with a mixture (e.g., a        solution) comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the device,        thereby generating the charged or zwitterion copolymer modified        device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        10,000 and about 250,000.

In another aspect, described herein is a method of preparing a chargedor zwitterion copolymer modified biofouling-resistant device comprising:

-   -   a) contacting a surface of a device with a mixture (e.g., a        solution) comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the device,        thereby generating the charged or zwitterion copolymer modified        device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        14,000 and about 21,000.

In yet another aspect, described herein is a method for synthesizing acompound of Formula (II) comprising: reacting a compound of Formula (IV)or a salt or solvate thereof with a compound of Formula (V):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OH,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   x is 0.001-0.999; and    -   wherein the compounds of Formula (II) and Formula (V) are each        independently charged or zwitterionic;    -   provided that a compound of Formula (II) is not

In another aspect, described herein is a method for synthesizing acompound of Formula (III) comprising: reacting a compound of Formula(IV) or a salt or solvate thereof with a compound of Formula (VI):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a); each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and        R^(6d) is independently selected from hydrogen, halogen, —CN,        —OR^(9a), optionally substituted C₁-C₄ alkyl, optionally        substituted C₁-C₄ fluoroalkyl, optionally substituted C₂-C₆        alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,        and —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   x is 0.001-0.999.

In one aspect, also described herein is a charged or zwitterioncopolymer modified biofouling-resistant device prepared by the methodcomprising:

-   -   a) contacting a surface of a silicon-based device with a mixture        (e.g., a solution) comprising a charged or zwitterion copolymer;        and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the        silicon-based device, thereby generating the charged or        zwitterion copolymer modified device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer.

In another aspect, described herein is a charged or zwitterion copolymermodified biofouling-resistant device prepared by the method comprising:

-   -   a) contacting a surface of a device with a mixture (e.g., a        solution) comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the device,        thereby generating the charged or zwitterion copolymer modified        device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        10,000 and about 250,000.

In another aspect, described herein is a charged or zwitterion copolymermodified biofouling-resistant device prepared by the method comprising:

-   -   c) contacting a surface of a device with a mixture (e.g., a        solution) comprising a charged or zwitterion copolymer; and    -   d) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the device,        thereby generating the charged or zwitterion copolymer modified        device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        14,000 and about 21,000.

BRIEF DESCRIPTION OF THE FIGURES

The accompanying figures, which are incorporated in and constitute apart of this specification, illustrate several aspects and together withthe description serve to explain and not to limit the scope of currentdisclosure.

FIG. 1 illustrates representative photografting of poly(sulfobetainemethacrylate-co-perfluorophenylazide methacrylate) (PFPA-PSB copolymer)to a silicone surface.

FIG. 2A illustrates representative water advancing contact angle (upperimage) and receding contact angle (lower image) on an unmodifiedsilicone surface and (b) PFPA-PSB copolymer modified silicone surface.

FIG. 2B illustrates representative water advancing contact angle (upperimage) and receding contact angle (lower image) on a PFPA-PSB copolymermodified silicone surface.

FIG. 3A illustrates high density of Escherichia coli adhesion tounmodified silicone surface forming an elastic film, which fracturedupon surface drying.

FIG. 3B illustrates very low density of Escherichia coli adhesion topoly(sulfobetaine methacrylate-co-perfluorophenylazidemethacrylate)-modified silicone surface.

FIG. 4 illustrates the structure of PFPA-PSB copolymer.

FIG. 5A illustrates chemical structure of polydimethylsiloxane andpolysulfobetaine.

FIG. 5B illustrates XPS spectra of a PFPA-PSB modified PDMS substrate,showing the successful grafting of PSB on the organic substrate.

Additional advantages of the invention will be set forth in part in thedescription which follows, and in part will be obvious from thedescription, or may be learned by practice of the invention. Theadvantages of the invention will be realized and attained by means ofthe elements and combinations particularly pointed out in the appendedclaims. It is to be understood that both the foregoing generaldescription and the following detailed description are exemplary andexplanatory only and are not restrictive of the invention, as claimed.

DETAILED DESCRIPTION

Hospital acquired infections (HAIs) cause over 100,000 deaths per yearand over $30 billion in direct healthcare cost. Despite reduction ofHAIs in recent years through improved antiseptic technique, surgicalprocedure, and diagnosis, HAIs declines are slowing down indicating theneed for new preventative methods. In some instances, medical devicesimplanted into the body are the source of infection. It is estimatedthat 60-70% of HAIs are associated with the use of implantable medicaldevices. Planktonic bacteria adhere to the surface of the medicaldevices and begin to grow into resilient biofilms that become moreresistant to antibiotics and disinfecting agents than in the planktonicstate. As the biofilm grows and the cells continue to proliferate, theextracellular matrix scaffolding (made up of proteins andpolysaccharides) bursts open, releasing more bacteria into the body. Thebody can no longer stave off infection and strong antibiotics must beused to fight the infectious cells. The use of strong antibiotics hasled to the existence of antibiotic resistant bacteria, also known assuperbugs, which can no longer be treated with conventional antibiotics.

Without the initial adhesion of planktonic cells to the surface of amaterial, the biofilm formation is prevented or reduced. Severalresearchers have identified the attractive forces that cause organicmaterial to adhere to polymeric surfaces: hydrophobic interactions andelectrostatic interactions (van der Waals forces) between the organicmaterials and polymer surface. Using self-assembled monolayers,Whitesides et al. surveyed several functional groups to determinesurface functionalities that promote or hinder the non-specificadsorption of proteins. (Whitesides, G. M. A survey ofstructure-property relationships of surfaces that resist the adsorptionof protein. Langmuir, 2001, 17 (18), pp 5605-5620). The functionalgroups that exhibited the lowest adhesion were electrostatically neutralhydrophilic moieties that contained hydrogen bond donating groups. Fromthese design rules, many material coatings have been developed and shownto reduce adhesion of proteins and microorganisms. However, thesecoating are substrate dependent and/or require exotic reactionconditions that are not compatible for wide-scale use. In some cases,several polymers coatings and surface modifications have been developedto repel these interactions to reduce/prevent the formation of biofilmson surfaces. In some instances, the coating should have the followingchemical requirements to be used as an anti-fouling surface: a) thecoating should be hydrophilic; b) the coating should consist of mostlyof hydrogen bond acceptors; and c) the coating should beelectrostatically neutral. However, due to the water-solubility ofhydrophilic coatings, the coating material should be covalently bound tothe polymeric material for long-term effects.

In some instances, medical grade silicone is used in medical and healthcare industry. Its market currently undergoes a rapid growth and isprojected to reach $7.23 billion by 2021. Medical grade siliconegenerally includes polydimethylsiloxane (PDMS) fluids and elastomers.Due to their good chemical stability, matching mechanical propertieswith human tissues, and no-requirements for plasticizers, PDMSelastomers generally have excellent biocompatibility, and are used inmedical devices and biomedical implants such as catheters andpacemakers. PDMS elastomers also have high transparency and easyprocessability. Therefore, PDMS elastomers have found broad applicationsin fabricating microfluidic devices, which provide low-cost, simple, androbust systems for diagnosing diseases (Whitesides, G. M. The originsand the future of microfluidics. Nature 2006, 442 (7101), 368-373).However, PDMS elastomers also have a low surface energy of about 20mN/m. Bacteria, platelets, proteins, and other biomolecules tend toadhere to the hydrophobic surfaces of PDMS elastomers (Hron, P.Hydrophilisation of silicone rubber for medical applications. Polymerinternational 2003, 52 (9), 1531-1539). For silicone medical implants,bacterial adhesion and biofilm formation may lead to the failure ofmedical devices, severe infection, and even death of patients. Fordisease diagnosis devices based on PDMS microfluidics, proteins andother biomolecules fouling on the PDMS surfaces can significantly reducethe sensitivity of these devices, and may even lead to completedevice-failure if blocking of the microfluidic channels occurs (Zhou, J.et al. Recent developments in PDMS surface modification for microfluidicdevices. Electrophoresis 2010, 31 (1), 2-16).

Hydrophilic treatment of the PDMS surfaces was found to be one of thestrategies to alleviate or prevent the problem of biofouling (Keefe, A.J. et al. Suppressing surface reconstruction of superhydrophobic PDMSusing a superhydrophilic zwitterionic polymer. Biomacromolecules 2012,13 (5), 1683-1687). Some conventional methods of making PDMS surfaceshydrophilic include oxidation of the surfaces by oxygen plasma,UV-ozone, or corona discharge. However, these modifications are onlytemporary because PDMS has an extremely low glass transition temperatureof about −120° C. and therefore the PDMS chains are highly mobile atroom temperature. The PDMS chains are able to rearrange and recover thehydrophobic surface of PDMS elastomers within a time window of a fewhours. In some cases, other methods seeking to make long-lastinghydrophilic PDMS surfaces take many steps and involve radical reactionor polymerization. These steps have to be performed in closedcontainers, and/or under the protection of inert gas. Due to the highersolubility of oxygen relative to nitrogen in PDMS, in some instances ittakes long time to remove oxygen from PDMS so that the radical reactioncan proceed efficiently. These strict reaction conditions significantlyincrease the cost and limit industrial applicability of these reactions.

In some embodiments, provided herein are biofouling-resistant coatingscomprising charged or zwitterion compounds comprising phenyl-azidemoieties. In some instances, biofouling comprises microfouling ormacrofouling. Microfouling comprises formation of microorganism adhesion(e.g., bacteria adhesion) and/or biofilm. Biofilm is a group ofmicroorganism which adheres to a surface. In some instances, the adheredmicroorganisms are further embedded in a self-produced matrix ofextracellular polymeric substance, which comprises a polymericconglomeration of extracellular DNA, protein, and polysaccharides.Macrofouling comprises attachment of larger organisms.

Charged and/or zwitterionic compounds bind water molecules viaelectrostatically induced hydration. In such cases, charged and/orzwitterionic materials exhibit surface resistance toprotein/cell/bacterial adhesion, biofilm formation, and/or macrofouling.In some embodiments, the charged or zwitterion compounds comprisecopolymers. In some embodiments, also provided herein are methods ofmaking biofouling-resistant coatings comprising charged or zwitterioncopolymers via polymerization reaction. In some embodiments, thepolymerization reaction is addition polymerization, atomic transferradical polymerization (ATRP), coordination polymerization, free-radicalpolymerization, nitroxide-mediated radical polymerization (NMP),reversible addition-fragmentation chain-transfer polymerization (RAFT),or ring-opening metathesis polymerization (ROMP). In some embodiments,the ionic polymerization is anionic polymerization or cationicpolymerization. In some embodiments, the polymerization reaction isreversible-deactivation polymerization (RDP). In some embodiments, thepolymerization reaction is free-radical polymerization. In someembodiments, the polymerization reaction is atomic transfer radicalpolymerization (ATRP). In some embodiments, biofouling-resistantcoatings comprising charged or zwitterion copolymers are grafted onto apolymer surface of a device under a UV exposure. In some otherembodiments, charged or zwitterion copolymers are grafted onto asilicone-comprising surface of a device under a UV exposure. In someembodiments, charged or zwitterion copolymers are grafted onto a surfaceof a medical device under a UV exposure. In some other embodiments,charged or zwitterion copolymers are grafted onto a silicone-comprisingsurface of a medical device under a UV exposure. In some embodiments,charged or zwitterion are grafted onto a polymer surface of a medicaldevice under a UV exposure. In some other embodiments, charged orzwitterion copolymers are grafted onto a silicone-comprising polymersurface of a medical device under a UV exposure.

In some embodiments, a charged or zwitterion copolymer modified devicecomprises anti-fouling properties and is used to prevent and/or toreduce the development of biofouling. In some embodiments, a charged orzwitterion copolymer modified medical device comprises anti-foulingproperties and is used to prevent and/or to reduce the development ofbiofouling. In some embodiments, the charged or zwitterion coatingsprevent and/or reduce the attachment of microorganisms, plants, algae,or animals to a surface.

In additional embodiments, disclosed herein are compounds to be used toprepare charged or zwitterion copolymers of the disclosure as well asthe charged or zwitterion copolymers themselves to be used within themethods disclosed herein.

I. Compounds

In one aspect, described herein is a compound that has the structure ofFormula (I) or a salt or solvate thereof:

-   -   wherein    -   A is selected from —C(═O)—, —S(═O)—, —S(═O)₂—, and        —S(═O)(—NR³)—;    -   L is selected from —OQ, —NR³Q, and —N(R³)₂Q⁺;    -   Q is a structure represented by a formula:

-   -   Z is selected from —CR^(6a)R^(6b)—, —C(═O)—, —C(═NH)—, and        —C(═NH)NR⁷—;    -   m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each R³ is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄ alkyl,        optionally substituted aryl, and —X-optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(4a), R^(4b), R^(5a), R^(5c), R^(6a) and R^(6b) is        independently selected from hydrogen, halogen, —CN, —OR⁹,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted aryl, —NR^(8a)R^(8b),        —NR^(8a)R^(8b)R^(8c), —S(═O)₂O⁻, —S(═O)₂OR⁹, —C(═O)O⁻, and        —C(═O)OR⁹;    -   R^(5b) is —OR^(10b), —NR^(10a)R^(10b), or        —NR^(10a)R^(10b)R^(10c+);    -   each R⁷, R^(8a), R^(8b), R^(8c), and R⁹ is independently        selected from hydrogen and optionally substituted C₁-C₄ alkyl,        and optionally substituted aryl;    -   each R^(10a) and R^(10c) is independently selected from        hydrogen, optionally substituted C₁-C₄ alkyl, optionally        substituted aryl, -(optionally substituted        C₁-C₈alkylene)S(═O)₂O⁻, -(optionally substituted        C₁-C₈alkylene)S(═O)₂OH, -(optionally substituted        C₁-C₈alkylene)C(═O)O⁻, and -(optionally substituted        C₁-C₈alkylene)C(═O)OH; and    -   R^(10b) is —C(═O)—C₂-C₆alkenyl, —S(═O)—C₂-C₆alkenyl, or        —S(═O)₂—C₂-C₆alkenyl.

In some embodiments, the compound of Formula (I) is not:

-   N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide;-   N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide; or-   2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

In some embodiments,N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamidehas a structure of:

In some embodiments,N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide has astructure of:

In some embodiments,N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide has astructure of:

In some embodiments, the compound of Formula (I) has a structureselected from:

In some embodiments, the compound of Formula (I) has the followingstructure:

In some embodiments, the compound of Formula (I) has a structureselected from:

In some embodiments, the compound of Formula (I) has a structureselected from:

In some embodiments, the compound of Formula (I) has a structureselected from:

In some embodiments, each R^(1a) and R^(1b) is independently halogen. Insome embodiments, each R^(1a) and R^(1b) is independently F or Cl. Insome embodiments, each R^(1a) and R^(1b) is F. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, andoptionally substituted C₁-C₆ fluoroalkyl. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, and —CF₃.In some embodiments, each R^(2a) and R^(2b) is independently selectedfrom F, Cl, —CN, and —CF₃. In some embodiments, each R^(2a) and R^(2b)is independently halogen. In some embodiments, each R^(2a) and R^(2b) isF. In some embodiments, each R^(2a) and R^(2b) is —CN. In someembodiments, each R^(2a) and R^(2b) is independently C₁-C₆ fluoroalkyl.In some embodiments, each R^(2a) and R^(2b) is —CF₃.

In some embodiments, each R^(1a), R^(1b), R^(2a), and R^(2b) is F.

In some embodiments, Z is selected from —CR^(6a)R^(6b)—, —C(═O)—,—C(═NH)—, and —C(═NH)NR⁷—. In some embodiments, Z is —CR^(6a)R^(6b)—. Insome embodiments, Z is —C(═O)—. In some embodiments, Z is —C(═NH)—. Insome embodiments, Z is —C(═NH)NR⁷—.

In some embodiments, each R³ is independently selected from hydrogen,optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄alkyl, optionally substituted aryl, and —X-optionally substituted aryl.In some embodiments, R³ is hydrogen. In some embodiments, R³ isoptionally substituted C₁-C₄ alkyl. In some embodiments, R³ is—X-optionally substituted C₁-C₄ alkyl. In some embodiments, R³ isoptionally substituted aryl. In some embodiments, R³ is —X-optionallysubstituted aryl.

In some embodiments, X is —C(═O)—, —S(═O)—, or —S(═O)₂—. In someembodiments, X is —C(═O)—. In some embodiments, X is —S(═O)—. In someembodiments, X is —S(═O)₂—.

In some embodiments, each R^(6a) and R^(6b) is hydrogen.

In some embodiments, m is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, mis 0, 1, 2, 3, 4, or 5. In some embodiments, m is 0, 1, 2, or 3. In someembodiments, m is 0. In some embodiments, m is 1. In some embodiments, mis 2. In some embodiments, m is 3. In some embodiments, m is 4. In someembodiments, m is 5.

In some embodiments, R^(5a) is hydrogen; R^(5b) is —NR^(10a)R^(10b); andR^(5c) is hydrogen.

In some embodiments, R^(5a) is hydrogen; R^(5b) is —OR^(10b); and R^(5c)is hydrogen.

In some embodiments, R^(4a) is hydrogen and R^(4b) is hydrogen.

In some embodiments, the compound of Formula (I) has a structure ofFormula (Ia):

In some embodiments, the compound of Formula (I) has a structure ofFormula (Ib):

In some embodiments, the compound of Formula (I) has a structure ofFormula (Ic):

In some embodiments, the compound of Formula (I) has a structure ofFormula (Id):

In some embodiments, R^(10a) is hydrogen, optionally substituted C₁-C₄alkyl, or optionally substituted aryl. In some embodiments, R^(10a) ishydrogen. In some embodiments, R^(10a) is optionally substituted C₁-C₄alkyl. In some embodiments, R^(10a) is CH₃. In some embodiments, R^(10a)is CH₂CH₃. In some embodiments, R^(10a) is optionally substituted aryl.In some embodiments, R^(10a) is phenyl.

In some embodiments, the compound of Formula (I) has a structure ofFormula (e):

In some embodiments, the compound of Formula (I) has a structure ofFormula (If):

In some embodiments, the compound of Formula (I) has a structure ofFormula (Ig):

In some embodiments, the compound of Formula (I) has a structure ofFormula (Ih):

In some embodiments, R^(10b) is —C(═O)—C₂-C₆alkenyl,—S(═O)—C₂-C₆alkenyl, or —S(═O)₂—C₂-C₆alkenyl. In some embodiments,R^(10b) is —C(═O)—C₂-C₆alkenyl. In some embodiments, R^(10b) is—(S═O)—C₂-C₆alkenyl. In some embodiments, R^(10b) is—S(═O)₂—C₂-C₆alkenyl.

In some embodiments, the compound of Formula (I) is selected from:

In some embodiments, the compound of Formula (I) is selected from:

In some embodiments, the compound of Formula (I) is selected from:

In some embodiments, the compound of Formula (I) is selected from:

In some embodiments, the compound of Formula (I) is selected from:

In some embodiments, the compound of Formula (I) is selected from:

In some embodiments, the compound of Formula (I) is selected from:

In some embodiments, the compound of Formula (I) is selected from:

In another aspect, described herein is a compound that has the structureof Formula (II) or a salt or solvate thereof:

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   0<x<1; and    -   wherein the compound of Formula (II) is charged or zwitterionic.

In some embodiments, a compound of Formula (II) is not

In some embodiments, x in Formula (II) is not about 0.9434.

In some embodiments, a compound of Formula (II) is not obtained by using2 g sulfobetaine methacrylate monomer and 156 mg perfluorophenylazidemethacrylamide monomer.

In some embodiments, each R^(1a) and R^(1b) is independently halogen. Insome embodiments, each R^(1a) and R^(1b) is independently F or Cl. Insome embodiments, each R^(1a) and R^(1b) is F. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, andoptionally substituted C₁-C₆ fluoroalkyl. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, and —CF₃.In some embodiments, each R^(2a) and R^(2b) is independently selectedfrom F, Cl, —CN, and —CF₃. In some embodiments, each R^(2a) and R^(2b)is independently halogen. In some embodiments, each R^(2a) and R^(2b) isF. In some embodiments, each R^(2a) and R^(2b) is —CN. In someembodiments, each R^(2a) and R^(2b) is independently C₁-C₆ fluoroalkyl.In some embodiments, each R^(2a) and R^(2b) is —CF₃.

In some embodiments, each R^(1a), R^(1b), R^(2a), and R^(2b) is F.

In some embodiments, A is —S(═O)₂—. In some embodiments, A is —C(═O)—.

In some embodiments, A² is —S(═O)₂—. In some embodiments, A² is —C(═O)—.

In some embodiments, A³ is —S(═O)₂—. In some embodiments, A³ is —C(═O)—.

In some embodiments, each B¹ and B² is —NR^(3c)—;

In some embodiments, each R^(3c) is independently hydrogen, optionallysubstituted C₁-C₄ alkyl, or optionally substituted aryl. In someembodiments, R^(3c) is hydrogen. In some embodiments, R^(3c) isoptionally substituted C₁-C₄ alkyl. In some embodiments, R^(3c) is —CH₃.In some embodiments, R^(3c) is optionally substituted aryl. In someembodiments, R^(3c) is optionally substituted phenyl.

In some embodiments, B³ is —O—.

In some embodiments, D is —S(═O)₂OR^(9a) or —C(═O)OR^(9a). In someembodiments, D is —S(═O)₂OR^(9a). In some embodiments, D is—C(═O)OR^(9a).

In some embodiments, R^(9a) is hydrogen or —CH₃. In some embodiments,R^(9a) is hydrogen. In some embodiments, R^(9a) is —CH₃.

In some embodiments, D is —S(═O)₂O⁻ or —C(═O)O⁻. In some embodiments, Dis —S(═O)₂O⁻.

In some embodiments, D is —C(═O)O⁻.

In some embodiments, each R^(6a) and R^(6d) is hydrogen.

In some embodiments, each R^(3a) and R^(3b) is independently hydrogen orC₁-C₄ alkyl. In some embodiments, each R^(3a) and R^(3b) isindependently hydrogen or —CH₃. In some embodiments, each R^(3a) andR^(3b) is hydrogen. In some embodiments, each R^(3a) and R^(3b) is —CH₃.

In some embodiments, each R^(4c) and R^(4d) is independently is hydrogenor —CH₃. In some embodiments, each R^(4c) and R^(4d) is hydrogen. Insome embodiments, each R^(4c) and R^(4d) is —CH₃. In some embodiments,R^(4c) is hydrogen and R^(4d) is —CH₃.

In some embodiments, each R^(5d) and R^(5e) is independently is hydrogenor —CH₃. In some embodiments, each R^(5d) and R^(5e) is hydrogen. Insome embodiments, each R^(5d) and R^(5e) is —CH₃. In some embodiments,R^(5d) is hydrogen and R^(5e) is —CH₃.

In some embodiments, R^(11a) is hydrogen or —CH₃. In some embodiments,R^(11a) is hydrogen. In some embodiments, R^(11a) is —CH₃.

In some embodiments, R^(12a) is hydrogen or —CH₃. In some embodiments,R^(12a) is hydrogen. In some embodiments, R^(12a) is —CH₃.

In some embodiments, each R^(11b), R^(11c), R^(12b), and R^(12c) ishydrogen.

In some embodiments, n is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, nis 0, 1, 2, 3, 4, or 5.

In some embodiments, n is 0. In some embodiments, n is 1. In someembodiments, n is 2. In some embodiments, n is 3. In some embodiments, nis 4. In some embodiments, n is 5.

In some embodiments, s is 1, 2, 3, or 4. In some embodiments, s is 1. Insome embodiments, s is 2. In some embodiments, s is 3. In someembodiments, s is 4.

In some embodiments, t is 1, 2, 3, or 4. In some embodiments, t is 1. Insome embodiments, t is 2. In some embodiments, t is 3. In someembodiments, t is 4.

In some embodiments, p is 1, 2, 3, or 4. In some embodiments, p is 1. Insome embodiments, p is 2. In some embodiments, p is 3. In someembodiments, p is 4.

In some embodiments, x is more than 0. In some embodiments, x is lessthan 1. In some embodiments, x is 0.0000001-0.9999999. In someembodiments, x is 0.00001-0.99999. In some embodiments, x is0.001-0.999. In some embodiments, x is 0.01-0.99. In some embodiments, xis 0.1-0.99. In some embodiments, x is 0.2-0.99. In some embodiments, xis 0.3-0.99. In some embodiments, x is 0.5-0.99. In some embodiments, xis 0.5-0.99. In some embodiments, x is 0.6-0.99. In some embodiments, xis 0.7-0.99. In some embodiments, x is 0.8-0.99. In some embodiments, xis 0.9-0.99. In some embodiments, x is 0.91-0.99. In some embodiments, xis 0.92-0.99.

In some embodiments, x is at least 0.0000001, at least 0.00001, at least0.001, at least 0.01, at least 0.02, at least 0.03, at least 0.04, atleast 0.05, at least 0.07, at least 0.09, at least 0.11, at least 0.15,at least 0.20, at least 0.23, at least 0.28, at least 0.35, at least0.42, at least 0.5, at least 0.53, at least 0.58, at least 0.63, atleast 0.67, at least 0.71, at least 0.75, at least 0.78, at least 0.79,at least 0.80, at least 0.81, at least 0.82, at least 0.83, at least0.84, at least 0.85, at least 0.86, at least 0.87, at least 0.88, atleast 0.89, at least 0.9, at least 0.91, at least 0.92, at least 0.93,at least 0.94, at least 0.95, at least 0.96, at least 0.97, at least0.98, or at least 0.99.

In some embodiments, x is at most 0.9999999, at most 0.99999, at most0.999, at most 0.99, at most 0.98, at most 0.97, at most 0.96, at most0.95, at most 0.94, at most 0.93, at most 0.92, at most 0.91, at most0.90, at most 0.89, at most 0.88, at most 0.87, at most 0.86, at most0.85, at most 0.84, at most 0.83, at most 0.82, at most 0.81, at most0.80, at most 0.79, at most 0.78, at most 0.77, at most 0.76, at most0.75, at most 0.74, at most 0.70, at most 0.66, at most 0.62, at most0.59, at most 0.56, at most 0.53, at most 0.50, at most 0.47, at most0.43, at most 0.39, at most 0.34, at most 0.29, at most 0.25, at most0.21, at most 0.18, at most 0.14, at most 0.10, at most 0.07, or at most0.04.

In some embodiments, x is about 0.89 to about 0.999. In someembodiments, x is at least about 0.89. In some embodiments, x is at mostabout 0.999. In some embodiments, x is about 0.89 to about 0.9, about0.89 to about 0.91, about 0.89 to about 0.92, about 0.89 to about 0.93,about 0.89 to about 0.94, about 0.89 to about 0.95, about 0.89 to about0.96, about 0.89 to about 0.97, about 0.89 to about 0.98, about 0.89 toabout 0.99, about 0.89 to about 0.999, about 0.9 to about 0.91, about0.9 to about 0.92, about 0.9 to about 0.93, about 0.9 to about 0.94,about 0.9 to about 0.95, about 0.9 to about 0.96, about 0.9 to about0.97, about 0.9 to about 0.98, about 0.9 to about 0.99, about 0.9 toabout 0.999, about 0.91 to about 0.92, about 0.91 to about 0.93, about0.91 to about 0.94, about 0.91 to about 0.95, about 0.91 to about 0.96,about 0.91 to about 0.97, about 0.91 to about 0.98, about 0.91 to about0.99, about 0.91 to about 0.999, about 0.92 to about 0.93, about 0.92 toabout 0.94, about 0.92 to about 0.95, about 0.92 to about 0.96, about0.92 to about 0.97, about 0.92 to about 0.98, about 0.92 to about 0.99,about 0.92 to about 0.999, about 0.93 to about 0.94, about 0.93 to about0.95, about 0.93 to about 0.96, about 0.93 to about 0.97, about 0.93 toabout 0.98, about 0.93 to about 0.99, about 0.93 to about 0.999, about0.94 to about 0.95, about 0.94 to about 0.96, about 0.94 to about 0.97,about 0.94 to about 0.98, about 0.94 to about 0.99, about 0.94 to about0.999, about 0.95 to about 0.96, about 0.95 to about 0.97, about 0.95 toabout 0.98, about 0.95 to about 0.99, about 0.95 to about 0.999, about0.96 to about 0.97, about 0.96 to about 0.98, about 0.96 to about 0.99,about 0.96 to about 0.999, about 0.97 to about 0.98, about 0.97 to about0.99, about 0.97 to about 0.999, about 0.98 to about 0.99, about 0.98 toabout 0.999, or about 0.99 to about 0.999. In some embodiments, x isabout 0.89, about 0.9, about 0.91, about 0.92, about 0.93, about 0.94,about 0.95, about 0.96, about 0.97, about 0.98, about 0.99, or about0.999.

In another aspect, described herein is a compound that has the structureof Formula (III) or a salt or solvate thereof:

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+)        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a); each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and        R^(6d) is independently selected from hydrogen, halogen, —CN,        —OR^(9a), optionally substituted C₁-C₄ alkyl, optionally        substituted C₁-C₄ fluoroalkyl, optionally substituted C₂-C₆        alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,        and —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   0<x<1.

In some embodiments, a compound of Formula (III) is charged orzwitterionic. In some embodiments, a compound of Formula (III) comprisesa positively charged repeating unit. In some embodiments a compound ofFormula (III) comprises a negatively charged repeating unit. In someembodiments, a compound of Formula (III) comprises positively chargedrepeating units and negatively charged repeating units. In someembodiments, the ratio of positively charged repeating units andnegatively charged repeating units in a compound of Formula (III) isfrom about 10:1 to about 1:10. In some embodiments, the ratio ofpositively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is from about 5:1 to about 1:5 Insome embodiments, the ratio of positively charged repeating units andnegatively charged repeating units in a compound of Formula (III) isfrom about 2:1 to about 1:2. In some embodiments, the ratio ofpositively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is about 1:1.

In some embodiments, each R^(1a) and R^(1b) is independently halogen. Insome embodiments, each R^(1a) and R^(1b) is independently F or Cl. Insome embodiments, each R^(1a) and R^(1b) is F. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, andoptionally substituted C₁-C₆ fluoroalkyl. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, and —CF₃.In some embodiments, each R^(2a) and R^(2b) is independently selectedfrom F, Cl, —CN, and —CF₃. In some embodiments, each R^(2a) and R^(2b)is independently halogen. In some embodiments, each R^(2a) and R^(2b) isF. In some embodiments, each R^(2a) and R^(2b) is —CN. In someembodiments, each R^(2a) and R^(2b) is independently C₁-C₆ fluoroalkyl.In some embodiments, each R^(2a) and R^(2b) is —CF₃.

In some embodiments, each R^(1a), R^(1b), R^(2a), and R^(2b) is F.

In some embodiments, A is —S(═O)₂—. In some embodiments, A is —C(═O)—.

In some embodiments, A² is —S(═O)₂—. In some embodiments, A² is —C(═O)—.

In some embodiments, A³ is —S(═O)₂—. In some embodiments, A³ is —C(═O)—.

In some embodiments, each B¹, B², and B³ is —NR^(3c)—.

In some embodiments, each R^(3c) is independently hydrogen, optionallysubstituted C₁-C₄ alkyl, or optionally substituted aryl. In someembodiments, R^(3c) is hydrogen. In some embodiments, R^(3c) isoptionally substituted C₁-C₄ alkyl. In some embodiments, R^(3c) is —CH₃.In some embodiments, R^(3c) is optionally substituted aryl. In someembodiments, R^(3c) is optionally substituted phenyl.

In some embodiments, E is —NR^(9a)R^(9b)R^(9c+) or —S(═O)₂OR^(9a).

In some embodiments, E is —NR^(9a)R^(9b)R^(9c+). In some embodiments,each R^(9a), R^(9b), and R^(9c) is independently hydrogen or C₁-C₄alkyl. In some embodiments, each R^(9a), R^(9b), and R^(9c) isindependently hydrogen or —CH₃. In some embodiments, R^(9a) is hydrogen.In some embodiments, R^(9a) is —CH₃. In some embodiments, R^(9b) ishydrogen. In some embodiments, R^(9b) is —CH₃. In some embodiments,R^(9c) is hydrogen. In some embodiments, R^(9c) is —CH₃.

In some embodiments, E is —S(═O)₂OR^(9a). In some embodiments, eachR^(9a) is hydrogen or —CH₃. In some embodiments, R^(9a) is hydrogen. Insome embodiments, R^(9a) is —CH₃.

In some embodiments, E is —S(═O)₂O⁻ or —C(═O)O⁻. In some embodiments, Eis —S(═O)₂O⁻.

In some embodiments, E is —C(═O)O⁻.

In some embodiments, each R^(6c) and R^(6d) is independently selectedfrom hydrogen and —CH₃.

In some embodiments, each R^(6c) and R^(6d) is hydrogen. In someembodiments, each R^(6c) and R^(6d) is —CH₃.

In some embodiments, each R^(4c) and R^(4d) is independently is hydrogenor —CH₃. In some embodiments, each R^(4c) and R^(4d) is hydrogen. Insome embodiments, each R^(4c) and R^(4d) is —CH₃. In some embodiments,R^(4c) is hydrogen and R^(4d) is —CH₃.

In some embodiments, each R^(5d) and R^(5e) is independently is hydrogenor —CH₃. In some embodiments, each R^(5d) and R^(5e) is hydrogen. Insome embodiments, each R^(5d) and R^(5e) is —CH₃. In some embodiments,R^(5d) is hydrogen and R^(5e) is —CH₃.

In some embodiments, R^(11a) is hydrogen or —CH₃. In some embodiments,R^(11a) is hydrogen. In some embodiments, R^(11a) is —CH₃.

In some embodiments, R^(12a) is hydrogen or —CH₃. In some embodiments,R^(12a) is hydrogen. In some embodiments, R^(12a) is —CH₃.

In some embodiments, each R^(11b), R^(11c), R^(12b), and R^(12c) ishydrogen.

In some embodiments, n is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, nis 0, 1, 2, 3, 4, or 5.

In some embodiments, n is 0. In some embodiments, n is 1. In someembodiments, n is 2. In some embodiments, n is 3. In some embodiments, nis 4. In some embodiments, n is 5.

In some embodiments, s is 1, 2, 3, or 4. In some embodiments, s is 1. Insome embodiments, s is 2. In some embodiments, s is 3. In someembodiments, s is 4.

In some embodiments, t is 1, 2, 3, or 4. In some embodiments, t is 1. Insome embodiments, t is 2. In some embodiments, t is 3. In someembodiments, t is 4.

In some embodiments, x is more than 0. In some embodiments, x is lessthan 1. In some embodiments, x is 0.0000001-0.9999999. In someembodiments, x is 0.00001-0.99999. In some embodiments, x is0.001-0.999. In some embodiments, x is 0.01-0.99. In some embodiments, xis 0.1-0.99. In some embodiments, x is 0.2-0.99. In some embodiments, xis 0.3-0.99. In some embodiments, x is 0.5-0.99. In some embodiments, xis 0.5-0.99. In some embodiments, x is 0.6-0.99. In some embodiments, xis 0.7-0.99. In some embodiments, x is 0.8-0.99. In some embodiments, xis 0.9-0.99. In some embodiments, x is 0.91-0.99. In some embodiments, xis 0.92-0.99.

In some embodiments, x is at least 0.0000001, at least 0.00001, at least0.001, at least 0.01, at least 0.02, at least 0.03, at least 0.04, atleast 0.05, at least 0.07, at least 0.09, at least 0.11, at least 0.15,at least 0.20, at least 0.23, at least 0.28, at least 0.35, at least0.42, at least 0.5, at least 0.53, at least 0.58, at least 0.63, atleast 0.67, at least 0.71, at least 0.75, at least 0.78, at least 0.79,at least 0.80, at least 0.81, at least 0.82, at least 0.83, at least0.84, at least 0.85, at least 0.86, at least 0.87, at least 0.88, atleast 0.89, at least 0.9, at least 0.91, at least 0.92, at least 0.93,at least 0.94, at least 0.95, at least 0.96, at least 0.97, at least0.98, or at least 0.99.

In some embodiments, x is at most 0.9999999, at most 0.99999, at most0.999, at most 0.99, at most 0.98, at most 0.97, at most 0.96, at most0.95, at most 0.94, at most 0.93, at most 0.92, at most 0.91, at most0.90, at most 0.89, at most 0.88, at most 0.87, at most 0.86, at most0.85, at most 0.84, at most 0.83, at most 0.82, at most 0.81, at most0.80, at most 0.79, at most 0.78, at most 0.77, at most 0.76, at most0.75, at most 0.74, at most 0.70, at most 0.66, at most 0.62, at most0.59, at most 0.56, at most 0.53, at most 0.50, at most 0.47, at most0.43, at most 0.39, at most 0.34, at most 0.29, at most 0.25, at most0.21, at most 0.18, at most 0.14, at most 0.10, at most 0.07, or at most0.04.

In some embodiments, x is about 0.89 to about 0.999. In someembodiments, x is at least about 0.89. In some embodiments, x is at mostabout 0.999. In some embodiments, x is about 0.89 to about 0.9, about0.89 to about 0.91, about 0.89 to about 0.92, about 0.89 to about 0.93,about 0.89 to about 0.94, about 0.89 to about 0.95, about 0.89 to about0.96, about 0.89 to about 0.97, about 0.89 to about 0.98, about 0.89 toabout 0.99, about 0.89 to about 0.999, about 0.9 to about 0.91, about0.9 to about 0.92, about 0.9 to about 0.93, about 0.9 to about 0.94,about 0.9 to about 0.95, about 0.9 to about 0.96, about 0.9 to about0.97, about 0.9 to about 0.98, about 0.9 to about 0.99, about 0.9 toabout 0.999, about 0.91 to about 0.92, about 0.91 to about 0.93, about0.91 to about 0.94, about 0.91 to about 0.95, about 0.91 to about 0.96,about 0.91 to about 0.97, about 0.91 to about 0.98, about 0.91 to about0.99, about 0.91 to about 0.999, about 0.92 to about 0.93, about 0.92 toabout 0.94, about 0.92 to about 0.95, about 0.92 to about 0.96, about0.92 to about 0.97, about 0.92 to about 0.98, about 0.92 to about 0.99,about 0.92 to about 0.999, about 0.93 to about 0.94, about 0.93 to about0.95, about 0.93 to about 0.96, about 0.93 to about 0.97, about 0.93 toabout 0.98, about 0.93 to about 0.99, about 0.93 to about 0.999, about0.94 to about 0.95, about 0.94 to about 0.96, about 0.94 to about 0.97,about 0.94 to about 0.98, about 0.94 to about 0.99, about 0.94 to about0.999, about 0.95 to about 0.96, about 0.95 to about 0.97, about 0.95 toabout 0.98, about 0.95 to about 0.99, about 0.95 to about 0.999, about0.96 to about 0.97, about 0.96 to about 0.98, about 0.96 to about 0.99,about 0.96 to about 0.999, about 0.97 to about 0.98, about 0.97 to about0.99, about 0.97 to about 0.999, about 0.98 to about 0.99, about 0.98 toabout 0.999, or about 0.99 to about 0.999. In some embodiments, x isabout 0.89, about 0.9, about 0.91, about 0.92, about 0.93, about 0.94,about 0.95, about 0.96, about 0.97, about 0.98, about 0.99, or about0.999.

In another aspect, described herein is a copolymer comprising:

a) a repeating unit of Formula (VII):

wherein

-   each R^(1a) and R^(1b) is independently selected from hydrogen and    halogen;-   each R^(2a) and R^(2b) is independently selected from halogen, —CN,    and optionally substituted C₁-C₆ fluoroalkyl;-   each A¹ and A² is independently selected from —C(═O)—, —S(═O)—,    —S(═O)₂—, and —S(═O)(═NR^(3c))—;-   each B¹ and B² is independently selected from —O— and —NR^(3c)—;    Z¹ is —(CR^(6c)R^(6d))_(s)—;    each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is    independently selected from hydrogen, halogen, —CN, —OR^(9a),    optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄    fluoroalkyl, optionally substituted C₂-C₆ alkenyl, —NR^(3c)R^(3d),    —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(11a), R^(11b), and R^(11c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and-   s is an integer selected from 1, 2, 3, 4, and 5;    b) a repeating unit of Formula (VIII):

wherein,

-   A³ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B³ is —O— or —NR^(3c)—;-   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);-   Z² is —(CR^(6c)R^(6d))_(t)—;-   Z³ is —(CR^(6c)R^(6d))_(p);-   each R^(3a) and R^(3b) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, and optionally substituted    benzyl;-   each R^(6c) and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(12a), R^(12b), and R^(12c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   t is an integer selected from 1, 2, 3, 4, or 5;-   p is an integer selected from 1, 2, 3, 4, or 5; and    wherein the repeating unit of Formula (VIII) is charged or    zwitterionic; and    c) a repeating unit of Formula (IX):

-   A⁴ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B⁴ is —O— or —NR^(3c)—;-   Z⁴ is —(CR^(6c)R^(6d))_(k)—;-   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c), optionally    substituted C₁-C₄ alkyl, optionally substituted C₁-C₆ fluoroalkyl,    —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);-   each R^(6c), and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(9b), R^(9c), R^(13a), R^(13b), and R^(13c) is    independently selected from hydrogen, optionally substituted C₁-C₄    alkyl, and optionally substituted aryl; and-   k is an integer selected from 1-10.

In some embodiments, the repeating unit of Formula (IX) is charged orzwitterionic.

In some embodiments, each R^(1a) and R^(1b) is independently halogen. Insome embodiments, each R^(1a) and R^(1b) is independently F or Cl. Insome embodiments, each R^(1a) and R^(1b) is F. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, andoptionally substituted C₁-C₆ fluoroalkyl. In some embodiments, eachR^(2a) and R^(2b) is independently selected from halogen, —CN, and —CF₃.In some embodiments, each R^(2a) and R^(2b) is independently selectedfrom F, Cl, —CN, and —CF₃. In some embodiments, each R^(2a) and R^(2b)is independently halogen. In some embodiments, each R^(2a) and R^(2b) isF. In some embodiments, each R^(2a) and R^(2b) is —CN. In someembodiments, each R^(2a) and R^(2b) is independently C₁-C₆ fluoroalkyl.In some embodiments, each R^(2a) and R^(2b) is —CF₃. In someembodiments, each R^(1a), R^(1b), R^(2a), and R^(2b) is F.

In some embodiments, A is —S(═O)₂—. In some embodiments, A is —C(═O)—.In some embodiments, A² is —S(═O)₂—. In some embodiments, A² is —C(═O)—.In some embodiments, A³ is —S(═O)₂—. In some embodiments, A³ is —C(═O)—.In some embodiments, A⁴ is —S(═O)₂—. In some embodiments, A⁴ is —C(═O)—.In some embodiments, A is —S(═O)₂— and each A², A³, and A⁴ is —C(═O)—.In some embodiments, each A¹, A², A³, and A⁴ is —C(═O)—.

In some embodiments, each B¹, B², and B³ is independently —O— or—NR^(3c)—. In some embodiments, B¹ is —O—. In some embodiments, B¹ is—NR^(3c)—. In some embodiments, B² is —O—. In some embodiments, B² is—NR^(3c)—. In some embodiments, B³ is —O—. In some embodiments, B³ is—NR^(3c)—. In some embodiments, B⁴ is —O—. In some embodiments, B⁴ is—NR^(3c).

In some embodiments, each R^(3c) is independently hydrogen, optionallysubstituted C₁-C₄ alkyl, or optionally substituted aryl. In someembodiments, R^(3c) is hydrogen. In some embodiments, R^(3c) isoptionally substituted C₁-C₄ alkyl. In some embodiments, R^(3c) is —CH₃.In some embodiments, each R^(3c) is hydrogen or —CH₃. In someembodiments, R^(3c) is optionally substituted aryl. In some embodiments,R^(3c) is optionally substituted phenyl.

In some embodiments, D is —S(═O)₂OR^(9a) or —C(═O)OR^(9a). In someembodiments, D is —S(═O)₂OR^(9a). In some embodiments, D is—C(═O)OR^(9a). In some embodiments, R^(9a) is hydrogen or —CH₃. In someembodiments, R^(9a) is hydrogen. In some embodiments, R^(9a) is —CH₃.

In some embodiments, D is —S(═O)₂O⁻ or —C(═O)O⁻. In some embodiments, Dis —S(═O)₂O⁻.

In some embodiments, D is —C(═O)O⁻.

In some embodiments, E is —NR^(9a)R^(9b)R^(9c+) or —S(═O)₂OR^(9a). Insome embodiments, E is —NR^(9a)R^(9b)R^(9c+) or —C(═O)OR^(9a).

In some embodiments, E is —NR^(9a)R^(9b)R^(9c+). In some embodiments,each R^(9a), R^(9b), and R^(9c) is independently hydrogen or C₁-C₄alkyl. In some embodiments, each R^(9a), R^(9b), and R^(9c) isindependently hydrogen or —CH₃. In some embodiments, R^(9a) is hydrogen.In some embodiments, R^(9a) is —CH₃. In some embodiments, R^(9b) ishydrogen. In some embodiments, R^(9b) is —CH₃. In some embodiments,R^(9c) is hydrogen. In some embodiments, R^(9c) is —CH₃.

In some embodiments, E is —S(═O)₂OR^(9a). In some embodiments, E is—C(═O)OR^(9a). In some embodiments, each R^(9a) is hydrogen or —CH₃. Insome embodiments, R^(9a) is hydrogen. In some embodiments, R^(9a) is—CH₃.

In some embodiments, E is —S(═O)₂O⁻ or —C(═O)O⁻. In some embodiments, Eis —S(═O)₂O⁻.

In some embodiments, E is —C(═O)O⁻.

In some embodiments, each R^(3a) and R^(3b) is independently hydrogen orC₁-C₄ alkyl. In some embodiments, each R^(3a) and R^(3b) isindependently hydrogen or —CH₃. In some embodiments, each R^(3a) andR^(3b) is hydrogen. In some embodiments, each R^(3a) and R^(3b) is —CH₃.

In some embodiments, each R^(4c) and R^(4d) is independently selectedfrom hydrogen and —CH₃.

In some embodiments, each R^(4c) and R^(4d) is hydrogen.

In some embodiments, each R^(5d) and R^(5e) is independently selectedfrom hydrogen and —CH₃.

In some embodiments, each R^(5d) and R^(5e) is hydrogen.

In some embodiments, each R^(4c), R^(4d), R^(5d), and R^(5e) isindependently hydrogen or —CH₃. In some embodiments, each R^(4c),R^(4d), R^(5d), and R^(5e) is hydrogen. In some embodiments, eachR^(4c), R^(4d), R^(5d), and R^(5e) is —CH₃.

In some embodiments, each R^(6c) and R^(6d) is independently selectedfrom hydrogen and —CH₃. In some embodiments, each R^(6c) and R^(6d) ishydrogen. In some embodiments, each R^(6c) and R^(6d) is —CH₃.

In some embodiments, each R^(3c) and R^(3d) is independently selectedfrom hydrogen and —CH₃.

In some embodiments, each R^(3c) and R^(3d) is hydrogen.

In some embodiments, each R^(3c), R^(3d), R^(6c), and R^(6d) isindependently hydrogen or —CH₃. In some embodiments, each R^(3c),R^(3d), R^(6c), and R^(6d) is hydrogen. In some embodiments, eachR^(3c), R^(3d), R^(6c), and R^(6d) is —CH₃.

In some embodiments, R^(11a) is hydrogen or —CH₃. In some embodiments,R^(11a) is hydrogen. In some embodiments, R^(11a) is —CH₃.

In some embodiments, R^(12a) is hydrogen or —CH₃. In some embodiments,R^(12a) is hydrogen. In some embodiments, R^(12a) is —CH₃.

In some embodiments, R^(13a) is hydrogen or —CH₃. In some embodiments,R^(13a) is hydrogen. In some embodiments, R^(13a) is —CH₃.

In some embodiments, each R^(11a), R^(12a), and R^(13a) is independentlyhydrogen or —CH₃. In some embodiments, each R^(11a), R^(12a), andR^(13a) is hydrogen. In some embodiments, each R^(11a), R^(12a), andR^(13a) is —CH₃.

In some embodiments, each R^(11b), R^(12a), R^(12b), R^(12c), R^(13b),and R^(13c) is hydrogen.

In some embodiments, n is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, nis 0, 1, 2, 3, 4, or 5.

In some embodiments, n is 0, 1, or 2. In some embodiments, n is 0. Insome embodiments, n is 1. In some embodiments, n is 2. In someembodiments, n is 3. In some embodiments, n is 4. In some embodiments, nis 5.

In some embodiments, s is 1, 2, 3, or 4. In some embodiments, s is 1. Insome embodiments, s is 2. In some embodiments, s is 3. In someembodiments, s is 4.

In some embodiments, t is 1, 2, 3, or 4. In some embodiments, t is 1. Insome embodiments, t is 2. In some embodiments, t is 3. In someembodiments, t is 4.

In some embodiments, p is 1, 2, 3, or 4. In some embodiments, p is 1. Insome embodiments, p is 2. In some embodiments, p is 3. In someembodiments, p is 4.

In some embodiments, k is 1, 2, 3, 4, or 5. In some embodiments, k is 1,2, 3, or 4. In some embodiments, k is 2, 3, or 4. In some embodiments, kis 2 or 3. In some embodiments, k is 1. In some embodiments, k is 2. Insome embodiments, k is 3. In some embodiments, k is 4.

In some embodiments, each s, t, p, and k is independently 1, 2, or 3. Insome embodiments, each s, t, p, and k is independently 1 or 2. In someembodiments, each s, t, p, and k is independently 2 or 3.

In some embodiments, a repeating unit of Formula (IX) comprises apositively charged repeating unit of Formula (IX). In some embodiments,a repeating unit of Formula (IX) comprises a negatively chargedrepeating unit of Formula (IX). In some embodiments, a copolymercomprising repeating units of Formula (VII), (VIII), and (IX) comprisesa positively charged repeating unit of Formula (IX) and a negativelycharged repeating unit of Formula (IX). In some embodiments, the ratioof positively charged repeating units of Formula (IX) and negativelycharged repeating units of Formula (IX) in a copolymer comprisingrepeating units of Formula (VII), (VIII), and (IX) is from about 10:1 toabout 1:10. In some embodiments, the ratio of positively chargedrepeating units of Formula (IX) and negatively charged repeating unitsof Formula (IX) in a copolymer comprising repeating units of Formula(VII), (VIII), and (IX) is from about 5:1 to about 1:5. In someembodiments, the ratio of positively charged repeating units of Formula(IX) and negatively charged repeating units of Formula (IX) in acopolymer comprising repeating units of Formula (VII), (VIII), and (IX)is from about 2:1 to about 1:2. In some embodiments, the ratio ofpositively charged repeating units of Formula (IX) and negativelycharged repeating units of Formula (IX) in a copolymer comprisingrepeating units of Formula (VII), (VIII), and (IX) is about 1:1.

In some embodiments, a copolymer comprising a repeating unit of Formula(VII), (VIII), and (IX) comprises the following number of monomer units:[(Formula (VII))a(Formula (VIII))b(Formula (IX))c], wherein each numbera, b, and c is independently selected from 1 to 1000. In someembodiments, each number a, b, and c is independently selected from 1 to100.

In some embodiments, a is from 1 to 10. In some embodiments, a is from 5to 10. In some embodiments, a is from 5 to 20. In some embodiments, a isat least 1, at least 2, at least 3, at least 4, at least 5, at least 6,at least 7, at least 8, at least 9, at least 10, at least 12, at least15, or at least 20. In some embodiments, a is at most 1, at most 2, atmost 3, at most 4, at most 5, at most 6, at most 7, at most 8, at most9, at most 10, at most 12, at most 15, or at most 20.

In some embodiments, b is from 5 to 75. In some embodiments, b is from10 to 100. In some embodiments, b is from 20 to 250. In someembodiments, b is from 50 to 500. In some embodiments, b is from 100 to1000. In some embodiments, b is at least 1, at least 5, at least 10, atleast 25, at least 50, at least 100, at least 200, at least 300, atleast 400, at least 500, at least 600, at least 700, at least 800, atleast 900, or at least 1000. In some embodiments, b is at most 1, atmost 5, at most 10, at most 25, at most 50, at most 100, at most 200, atmost 300, at most 400, at most 500, at most 600, at most 700, at most800, at most 900, or at most 1000.

In some embodiments, c is from 5 to 75. In some embodiments, c is from10 to 100. In some embodiments, c is from 20 to 250. In someembodiments, c is from 50 to 500. In some embodiments, c is from 100 to1000. In some embodiments, c is at least 1, at least 5, at least 10, atleast 25, at least 50, at least 100, at least 200, at least 300, atleast 400, at least 500, at least 600, at least 700, at least 800, atleast 900, or at least 1000. In some embodiments, c is at most 1, atmost 5, at most 10, at most 25, at most 50, at most 100, at most 200, atmost 300, at most 400, at most 500, at most 600, at most 700, at most800, at most 900, or at most 1000.

In some embodiments, the ratio of (b+c) to a is from 1:1000 to 1000:1.In some embodiments, the ratio of (b+c) to a is from 1:100 to 100:1. Insome embodiments, the ratio of (b+c) to a is from 1:10 to 10:1. In someembodiments, the ratio of (b+c) to a is about 5:1, about 10:1, about20:1, about 30:1, about 40:1, about 50:1, about 75:1, about 100:1, about250:1, about 500:1, about 750:1, or about 1000:1.

In some embodiments, different variables of a compound of Formula (I),Formula (II), Formula (III), Formula (VII), Formula (VIII), and Formula(IX) as described above are applicable to the corresponding Formulas,compositions, membranes, devices, etc. disclosed throughout theapplication.

Any combination of the groups described above or below for the variousvariables is contemplated herein. Throughout the specification, groupsand substituents thereof are chosen by one skilled in the field toprovide stable moieties and compounds.

Further Forms of Compounds

In one aspect, the compound of Formula (I), (II), (III), (IV), (V), or(VI), or the copolymer comprising a repeating unit of Formula (VII),(VIII), and (IX) possesses one or more stereocenters and eachstereocenter exists independently in either the R or S configuration.The compounds presented herein include all diastereomeric, enantiomeric,and epimeric forms as well as the appropriate mixtures thereof. Thecompounds and methods provided herein include all cis, trans, syn, anti,entgegen (E), and zusammen (Z) isomers as well as the appropriatemixtures thereof. In certain embodiments, compounds described herein areprepared as their individual stereoisomers by reacting a racemic mixtureof the compound with an optically active resolving agent to form a pairof diastereoisomeric compounds/salts, separating the diastereomers andrecovering the optically pure enantiomers. In some embodiments,resolution of enantiomers is carried out using covalent diastereomericderivatives of the compounds described herein. In another embodiment,diastereomers are separated by separation/resolution techniques basedupon differences in solubility. In other embodiments, separation ofstereoisomers is performed by chromatography or by the formingdiastereomeric salts and separation by recrystallization, orchromatography, or any combination thereof. Jean Jacques, Andre Collet,Samuel H. Wilen, “Enantiomers, Racemates and Resolutions”, John WileyAnd Sons, Inc., 1981. In one aspect, stereoisomers are obtained bystereoselective synthesis.

In another embodiment, the compounds described herein are labeledisotopically (e.g. with a radioisotope) or by another other means,including, but not limited to, the use of chromophores or fluorescentmoieties, bioluminescent labels, or chemiluminescent labels.

Compounds described herein include isotopically-labeled compounds, whichare identical to those recited in the various formulae and structurespresented herein, but for the fact that one or more atoms are replacedby an atom having an atomic mass or mass number different from theatomic mass or mass number usually found in nature. Examples of isotopesthat can be incorporated into the present compounds include isotopes ofhydrogen, carbon, nitrogen, oxygen, sulfur, fluorine and chlorine, suchas, for example, ²H, ³H, ¹³C, ¹⁴C, ¹⁵N, ¹⁸O, ¹⁷O, ³⁵S, ¹⁸F, ³⁶Cl. In oneaspect, isotopically-labeled compounds described herein, for examplethose into which radioactive isotopes such as ³H and ¹⁴C areincorporated, are useful in drug and/or substrate tissue distributionassays. In one aspect, substitution with isotopes such as deuteriumaffords certain therapeutic advantages resulting from greater metabolicstability, such as, for example, increased in vivo half-life or reduceddosage requirements.

Compounds described herein might be formed as, and/or used as, salts.The type of salts, include, but are not limited to: (1) acid additionsalts, formed by reacting the free base form of the compound with:inorganic acid, such as, for example, hydrochloric acid, hydrobromicacid, sulfuric acid, phosphoric acid, metaphosphoric acid, and the like;or with an organic acid, such as, for example, acetic acid, propionicacid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvicacid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid,fumaric acid, trifluoroacetic acid, tartaric acid, citric acid, benzoicacid, 3-(4-hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid,methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid,2-hydroxyethanesulfonic acid, benzenesulfonic acid, toluenesulfonicacid, 2-naphthalenesulfonic acid,4-methylbicyclo-[2.2.2]oct-2-ene-1-carboxylic acid, glucoheptonic acid,4,4′-methylenebis-(3-hydroxy-2-ene-1-carboxylic acid), 3-phenylpropionicacid, trimethylacetic acid, tertiary butylacetic acid, lauryl sulfuricacid, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylicacid, stearic acid, muconic acid, butyric acid, phenylacetic acid,phenylbutyric acid, valproic acid, and the like; (2) salts formed whenan acidic proton present in the parent compound is replaced by a metalion, e.g., an alkali metal ion (e.g. lithium, sodium, potassium), analkaline earth ion (e.g. magnesium, or calcium), or an aluminum ion. Insome cases, compounds described herein may coordinate with an organicbase, such as, but not limited to, ethanolamine, diethanolamine,triethanolamine, tromethamine, N-methylglucamine, dicyclohexylamine,tris(hydroxymethyl)methylamine. In other cases, compounds describedherein may form salts with amino acids such as, but not limited to,arginine, lysine, and the like. Acceptable inorganic bases used to formsalts with compounds that include an acidic proton, include, but are notlimited to, aluminum hydroxide, calcium hydroxide, potassium hydroxide,sodium carbonate, sodium hydroxide, and the like.

It should be understood that a reference to a salt includes the solventaddition forms, particularly solvates. Solvates contain eitherstoichiometric or non-stoichiometric amounts of a solvent, such aswater, ethanol, and the like. Hydrates are formed when the solvent iswater, or alcoholates are formed when the solvent is alcohol. Solvatesof compounds described herein can be conveniently prepared or formedduring the processes described herein. In addition, the compoundsprovided herein can exist in unsolvated as well as solvated forms. Ingeneral, the solvated forms are considered equivalent to the unsolvatedforms for the purposes of the compounds and methods provided herein.

Synthesis of Compounds

Compounds described herein are synthesized using standard synthetictechniques or using methods known in the art in combination with methodsdescribed herein.

Unless otherwise indicated, conventional methods of mass spectroscopy,NMR, HPLC, protein chemistry, biochemistry, recombinant DNA techniquesand pharmacology are employed.

Compounds are prepared using standard organic chemistry techniques suchas those described in, for example, March's Advanced Organic Chemistry,6th Edition, John Wiley and Sons, Inc. Alternative reaction conditionsfor the synthetic transformations described herein may be employed suchas variation of solvent, reaction temperature, reaction time, as well asdifferent chemical reagents and other reaction conditions. The startingmaterials are available from commercial sources or are readily prepared.

Suitable reference books and treatise that detail the synthesis ofreactants useful in the preparation of compounds described herein, orprovide references to articles that describe the preparation, includefor example, “Synthetic Organic Chemistry”, John Wiley & Sons, Inc., NewYork; S. R. Sandler et al., “Organic Functional Group Preparations,” 2ndEd., Academic Press, New York, 1983; H. O. House, “Modern SyntheticReactions”, 2nd Ed., W. A. Benjamin, Inc. Menlo Park, Calif. 1972; T. L.Gilchrist, “Heterocyclic Chemistry”, 2nd Ed., John Wiley & Sons, NewYork, 1992; J. March, “Advanced Organic Chemistry: Reactions, Mechanismsand Structure”, 4th Ed., Wiley Interscience, New York, 1992. Additionalsuitable reference books and treatise that detail the synthesis ofreactants useful in the preparation of compounds described herein, orprovide references to articles that describe the preparation, includefor example, Fuhrhop, J. and Penzlin G. “Organic Synthesis: Concepts,Methods, Starting Materials”, Second, Revised and Enlarged Edition(1994) John Wiley & Sons ISBN: 3 527-29074-5; Hoffman, R. V. “OrganicChemistry, An Intermediate Text” (1996) Oxford University Press, ISBN0-19-509618-5; Larock, R. C. “Comprehensive Organic Transformations: AGuide to Functional Group Preparations” 2nd Edition (1999) Wiley-VCH,ISBN: 0-471-19031-4; March, J. “Advanced Organic Chemistry: Reactions,Mechanisms, and Structure” 4th Edition (1992) John Wiley & Sons, ISBN:0-471-60180-2; Otera, J. (editor) “Modern Carbonyl Chemistry” (2000)Wiley-VCH, ISBN: 3-527-29871-1; Patai, S. “Patai's 1992 Guide to theChemistry of Functional Groups” (1992) Interscience ISBN: 0-471-93022-9;Solomons, T. W. G. “Organic Chemistry” 7th Edition (2000) John Wiley &Sons, ISBN: 0-471-19095-0; Stowell, J. C., “Intermediate OrganicChemistry” 2nd Edition (1993) Wiley-Interscience, ISBN: 0-471-57456-2;“Industrial Organic Chemicals: Starting Materials and Intermediates: AnUllmann's Encyclopedia” (1999) John Wiley & Sons, ISBN: 3-527-29645-X,in 8 volumes; “Organic Reactions” (1942-2000) John Wiley & Sons, in over55 volumes; and “Chemistry of Functional Groups” John Wiley & Sons, in73 volumes.

In the reactions described, it may be necessary to protect reactivefunctional groups, for example hydroxy, amino, imino, thio or carboxygroups, where these are desired in the final product, in order to avoidtheir unwanted participation in reactions. A detailed description oftechniques applicable to the creation of protecting groups and theirremoval are described in Greene and Wuts, Protective Groups in OrganicSynthesis, 3rd Ed., John Wiley & Sons, New York, N.Y., 1999, andKocienski, Protective Groups, Thieme Verlag, New York, N.Y., 1994, whichare incorporated herein by reference for such disclosure).

In some embodiments, compounds are synthesized as described in theExamples section.

II. Biofouling-Resistant Coatings

In one aspect, described herein is a biofouling-resistant coatingcomprising a compound of Formula (I):

-   -   wherein    -   A is selected from —C(═O)—, —S(═O)—, —S(═O)₂—, and        —S(═O)(—NR³)—;    -   L is selected from —OQ, —NR³Q, and —N(R³)₂Q⁺;    -   Q is a structure represented by a formula:

-   -   Z is selected from —CR^(6a)R^(6b)—, —C(═O)—, —C(═NH)—, and        —C(═NH)NR⁷—;    -   m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each R³ is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄ alkyl,        optionally substituted aryl, and —X-optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(4a), R^(4b), R^(5a), R^(5c), R^(6a), and R^(6b) is        independently selected from hydrogen, halogen, —CN, —OR⁹,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted aryl, —NR^(8a)R^(8b),        —NR^(8a)R^(8b)R^(8c+), —S(═O)₂O⁻, —S(═O)₂OR⁹, —C(═O)O⁻, and        —C(═O)OR⁹;    -   R^(5b) is —OR^(10b), —NR^(10a)R^(10b), or        —NR^(10a)R^(10b)R^(10c);    -   each R⁷, R^(8a), R^(8b), R^(8c), and R⁹ is independently        selected from hydrogen and optionally substituted C₁-C₄ alkyl,        and optionally substituted aryl;    -   each R^(10a) and R^(10c) is independently selected from        hydrogen, optionally substituted C₁-C₄ alkyl, optionally        substituted aryl, -(optionally substituted        C₁-C₈alkylene)S(═O)₂O⁻, -(optionally substituted        C₁-C₈alkylene)S(═O)₂OH, -(optionally substituted        C₁-C₈alkylene)C(═O)O⁻, and -(optionally substituted        C₁-C₈alkylene)C(═O)OH; and    -   R^(10b) is —C(═O)—C₂-C₆alkenyl, —S(═O)—C₂-C₆alkenyl, or        —S(═O)₂—C₂-C₆alkenyl.

In some embodiments, the compound of Formula (I) is not:

-   -   N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide;    -   N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide; or    -   2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

In some embodiments, the biofouling-resistant coating comprising acompound of Formula (I), comprises a residue of the compound of Formula(I). In some embodiments, the residue of a compound of Formula (I)comprises a singlet nitrene residue.

In some embodiments, the compound of Formula (I) has a structure asdescribed above.

In some embodiments, different variables of a compound of Formula (I)are as described above.

In some embodiments, the compound of Formula (I) has a structure ofFormula (Ia), Formula (Ib), Formula (Ic), Formula (Id), Formula (Ie),Formula (If), Formula (Ig), or Formula (Ih) as described above.

In some embodiments, the compound of Formula (I) is selected fromcompounds as described above.

In another aspect, described herein is a biofouling-resistant coatingcomprising a compound of Formula (II):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   0<x<1; and    -   wherein the compound of Formula (II) is charged or zwitterionic.

In some embodiments, a compound of Formula (II) is not

In some embodiments, x in Formula (II) is not about 0.9434.

In some embodiments, a compound of Formula (II) is not obtained by using2 g sulfobetaine methacrylate monomer and 156 mg perfluorophenylazidemethacrylamide monomer.

In some embodiments, different variables of a compound of Formula (II)are as described above.

In another aspect, described herein is a biofouling-resistant coatingcomprising a compound of Formula (III):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+)        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a);    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c), is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   0<x<1.

In some embodiments, a compound of Formula (III) is charged orzwitterionic. In some embodiments, a compound of Formula (III) comprisesa positively charged repeating unit. In some embodiments a compound ofFormula (III) comprises a negatively charged repeating unit. In someembodiments, a compound of Formula (III) comprises positively chargedrepeating units and negatively charged repeating units. In someembodiments, the ratio of positively charged repeating units andnegatively charged repeating units in a compound of Formula (III) isfrom about 10:1 to about 1:10. In some embodiments, the ratio ofpositively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is from about 5:1 to about 1:5 Insome embodiments, the ratio of positively charged repeating units andnegatively charged repeating units in a compound of Formula (III) isfrom about 2:1 to about 1:2. In some embodiments, the ratio ofpositively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is about 1:1.

In some embodiments, different variables of a compound of Formula (III)are as described above.

In another aspect, described herein is a biofouling-resistant coatingcomprising a copolymer, comprising:

a) a repeating unit of Formula (VII):

wherein

-   each R^(1a) and R^(1b) is independently selected from hydrogen and    halogen;-   each R^(2a) and R^(2b) is independently selected from halogen, —CN,    and optionally substituted C₁-C₆ fluoroalkyl;-   each A¹ and A² is independently selected from —C(═O)—, —S(═O)—,    —S(═O)₂—, and —S(═O)(═NR^(3c))—;-   each B¹ and B² is independently selected from —O— and —NR^(3c)—;-   Z¹ is —(CR^(6c)R^(6d))_(s)—;-   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is    independently selected from hydrogen, halogen, —CN, —OR^(9a),    optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄    fluoroalkyl, optionally substituted C₂-C₆ alkenyl, —NR^(3c)R^(3d),    —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(11a), R^(11b), and R^(11c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and-   s is an integer selected from 1, 2, 3, 4, and 5;-   b) a repeating unit of Formula (VIII):

wherein,

-   A³ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B³ is —O— or —NR^(3c)—;-   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);-   Z² is —(CR^(6c)R^(6d))_(t)—;-   Z³ is —(CR^(6c)R^(6d))_(p);-   each R^(3a) and R^(3b) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, and optionally substituted    benzyl;-   each R^(6c) and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(12a), R^(12b), and R^(12c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   t is an integer selected from 1, 2, 3, 4, or 5;-   p is an integer selected from 1, 2, 3, 4, or 5; and    wherein the repeating unit of Formula (VIII) is charged or    zwitterionic; and    c) a repeating unit of Formula (IX):

-   A⁴ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B⁴ is —O— or —NR^(3c)—;-   Z⁴ is —(CR^(6c)R^(6d))_(k)—;-   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+) optionally    substituted C₁-C₄ alkyl, optionally substituted-   C₁-C₆ fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or    —C(═O)OR^(9a);-   each R^(6c), and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(9b), R^(9c), R^(13a), R^(13b), and R^(13c) is    independently selected from hydrogen, optionally substituted C₁-C₄    alkyl, and optionally substituted aryl; and-   k is an integer selected from 1-10.

In some embodiments, the repeating unit of Formula (IX) is charged orzwitterionic.

In some embodiments, different variables of a compound of Formula (VII),Formula (VIII), and Formula (IX) are as described above.

Any combination of the groups described above or below for the variousvariables is contemplated herein. Throughout the specification, groupsand substituents thereof are chosen by one skilled in the field toprovide stable moieties and compounds.

In some embodiments, the biofouling-resistant coating described hereincomprises one or more compounds of Formula (I), (II), or (III).

In some embodiments, the biofouling-resistant coating described hereincomprises one or more copolymers of Formula (II) or (III). In someembodiments, the biofouling-resistant coating described herein comprisesone or more copolymers comprising repeating units of Formula (VII),(VIII), and (IX).

In some embodiments, the biofouling-resistant coating comprising one ormore compounds of Formula (I), (II), and (III) is applied onto a surfaceof the device. In some embodiments, the biofouling-resistant coatingcomprising one or more copolymers comprising repeating units of Formula(VII), (VIII), and (IX) is applied onto a surface of the device. In someembodiments, the surface of the device comprises a polymer. In someembodiments, the polymer is selected from polysiloxanes, polyurethanes,polyamides, polyimides, epoxy resins, polyesters, polyolefins,polysulfones, polycarbonates, polyvinylchloride, polyvinylidenedifluoride, polyethers, polyether terpthalate, or a mixture thereof.

III. Devices

In certain embodiments, provided herein are devices coated by one ormore compounds described herein. In some embodiments, the devices aremedical devices. In some embodiments, the devices are non-medicaldevices. In some instances, provided herein are medical devices coatedby one or more compounds described herein. In other instances, providedherein are non-medical devices coated by one or more compounds describedherein. In additional instances, provided herein are devices coated byone or more compounds described herein in which the coated devicereduces the potential for infection.

In some embodiments, the device comprises a polymer-based device. Insome embodiments, the polymer-based device comprises a polyolefinicdevice. In some embodiments, the polyolefinic device comprises a devicemodified with polyethylene (PE), polypropylene (PP), polyamide (PA),polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVdF),polyvinyl chloride (PVC), or a combination thereof. In some embodiments,the device comprises a microporous device or a nonwoven device. In someembodiments, the device comprises a carbon-based device comprising amoiety capable of binding with a compound that has a structure ofFormula (I), (II), or (III). In some embodiments, the device comprises acarbon-based device comprising a moiety capable of binding with acopolymer comprising a repeating unit of Formula (VII), (VIII), and(IX). In some embodiments, the carbon-based device comprises a polymermoiety. In some embodiments, the carbon-based device comprises acarbon-based polymer. In some embodiments, the carbon-based devicecomprises a polyolefin moiety. In some embodiments, the polyolefinmoiety comprises a polyethylene (PE) moiety, a polypropylene (PP)moiety, a polyamide (PA) moiety, a polytetrafluoroethylene (PTFE)moiety, a polyvinylidene fluoride (PVdF) moiety, or a polyvinyl chloride(PVC) moiety.

In some embodiments, the device comprises a carbon-based device. In someembodiments, the carbon-based device comprises a carbon-based polymer.In some embodiments, the carbon-based device comprises a polyolefinmoiety. In some embodiments, the polyolefin moiety comprisespolyethylene moiety, polypropylene moiety, polyvinyl chloride moiety,polyvinylidene fluoride moiety, polytetrafluoroethylene moiety,polychlorotrifluoroethylene moiety, or polystyrene moiety.

In some embodiments, the carbon-based polymer comprises polyamidemoiety, polyurethane moiety, phenol-formaldehyde resin moiety,polycarbonate moiety, polychloroprene moiety, polyacrylonitrile moiety,polyimide moiety, or polyester moiety. In some embodiments, thecarbon-based polymer comprises nylon. In some embodiments, thecarbon-based polymer comprises polyethylene terephthalate.

In some embodiments, the device comprises a silicon-based device. Insome embodiments, the silicon-based device comprises a silicon-basedpolymer moiety. In some embodiments, the device comprises asilicon-based device comprising a moiety capable of binding with acompound that has a structure of Formula (I), (II), or (III). In someembodiments, the device comprises a silicon-based device comprising amoiety capable of binding with a copolymer comprising a repeating unitof Formula (VII), (VIII), and (IX). In some embodiments, thesilicon-based device comprises a polymer moiety. In some embodiments,the silicon-based device comprises a siloxane polymer moiety, asesquisiloxane polymer moiety, a siloxane-silarylene polymer moiety, asilalkylene polymer moiety, a polysilane moiety, a polysilylene moiety,or a polysilazane moiety.

In some embodiments, the silicon-based device comprises a siloxanepolymer moiety. In some embodiments, the silicon-based device comprisessilicone polymer. In some embodiments, the silicon-based devicecomprises a silicone-based device.

In some embodiments, the device comprises a carbon-based device or asilicon-based device.

In some embodiments, a device described herein coated by a compounddescribed herein leads to a reduced potential for infection relative toa device not coated by the compound. In some instances, the reducedpotential for infection is by about 10%, 20%, 30%, 40%, 50%, 60%, 70%,80%, 90%, 95%, 99%, 99.5%, 99.9%, or more relative to a device notcoated by the compound. In some instances, the reduced potential forinfection is by about 10%, or more relative to a device not coated bythe compound. In some instances, the reduced potential for infection isby about 20%, or more relative to a device not coated by the compound.In some instances, the reduced potential for infection is by about 30%,or more relative to a device not coated by the compound. In someinstances, the reduced potential for infection is by about 40%, or morerelative to a device not coated by the compound. In some instances, thereduced potential for infection is by about 50%, or more relative to adevice not coated by the compound. In some instances, the reducedpotential for infection is by about 60%, or more relative to a devicenot coated by the compound. In some instances, the reduced potential forinfection is by about 70%, or more relative to a device not coated bythe compound. In some instances, the reduced potential for infection isby about 80%, or more relative to a device not coated by the compound.In some instances, the reduced potential for infection is by about 90%,or more relative to a device not coated by the compound. In someinstances, the reduced potential for infection is by about 95%, or morerelative to a device not coated by the compound. In some instances, thereduced potential for infection is by about 99%, or more relative to adevice not coated by the compound. In some instances, the reducedpotential for infection is by about 99.5%, or more relative to a devicenot coated by the compound. In some instances, the reduced potential forinfection is by about 99.9%, or more relative to a device not coated bythe compound.

Medical Devices

In some embodiments, a device described herein is a medical device. Insome cases, a medical device described herein comprises a dentalinstrument or a medical instrument. In some instances, a medical devicecomprises an implant, an IV, a prosthesis, a suturing material, a valve,a stent, a catheter, a rod, a shunt, a scope, a contact lens, a tubing,a wiring, an electrode, a clip, a fastener, a syringe, a container, or acombination thereof. In some embodiments, a medical device comprises animplant. In some embodiments, a medical device comprises an IV. In someembodiments, a medical device comprises a prosthesis. In someembodiments, a medical device comprises a suturing material. In someembodiments, a medical device comprises a valve. In some embodiments, amedical device comprises a stent. In some embodiments, a medical devicecomprises a catheter. In some embodiments, a medical device comprises arod. In some embodiments, a medical device comprises a shunt. In someembodiments, a medical device comprises a scope. In some embodiments, amedical device comprises a contact lens. In some embodiments, a medicaldevice comprises a tubing. In some embodiments, a medical devicecomprises a wiring. In some embodiments, a medical device comprises anelectrode. In some embodiments, a medical device comprises a clip. Insome embodiments, a medical device comprises a fastener. In someembodiments, a medical device comprises a syringe. In some embodiments,a medical device comprises a container. In some instances, a devicedescribed herein comprises a dental instrument or a medical instrument.In some instances, a device described herein comprises an implant, anIV, a prosthesis, a suturing material, a valve, a stent, a catheter, arod, a shunt, a scope, a contact lens, a tubing, a wiring, an electrode,a clip, a fastener, a syringe, a container, or a combination thereof. Insome embodiments, a device comprises an implant. In some embodiments, adevice comprises an IV. In some embodiments, a device comprises aprosthesis. In some embodiments, a device comprises a suturing material.In some embodiments, a device comprises a valve. In some embodiments, adevice comprises a stent. In some embodiments, a device comprises acatheter. In some embodiments, a device comprises a rod. In someembodiments, a device comprises a shunt. In some embodiments, a devicecomprises a scope. In some embodiments, a device comprises a contactlens. In some embodiments, a device comprises a tubing. In someembodiments, a device comprises a wiring. In some embodiments, a devicecomprises an electrode. In some embodiments, a device comprises a clip.In some embodiments, a device comprises a fastener. In some embodiments,a device comprises a syringe. In some embodiments, a device comprises acontainer.

In some embodiments, a compound described herein is coated onto amedical device. In some instances, a compound described herein is coatedonto a medical device to prevent and/or reduce biofouling (e.g.,microfouling such as bacteria adhesion or biofilm). In some instances, acompound described herein is coated onto a dental instrument or amedical instrument to prevent and/or reduce biofouling (e.g.,microfouling such as bacteria adhesion or biofilm). In some instances, acompound described herein is coated onto an implant, an IV, aprosthesis, a suturing material, a valve, a stent, a catheter, a rod, ashunt, a scope, a contact lens, a tubing, a wiring, an electrode, aclip, a fastener, a syringe, a container, or a combination thereof toprevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm).

In some cases, a device described herein comprises a catheter. In somecases, a catheter comprises an indwelling catheter. In some instances, acatheter comprises a permcath. In some instances, a catheter comprises auretic catheter or a Foley catheter.

In some instances, a compound described herein is coated onto a catheterto prevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto an indwelling catheter to prevent and/or reduce biofouling(e.g., microfouling such as bacteria adhesion or biofilm). In someinstances, a compound described herein is coated onto a permcath toprevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto a uretic catheter to prevent and/or reduce biofouling (e.g.,microfouling such as bacteria adhesion or biofilm). In some instances, acompound described herein is coated onto a Foley catheter to preventand/or reduce biofouling (e.g., microfouling such as bacteria adhesionor biofilm).

In some instances, a device described herein comprises an implant. Insome instances, an implant comprises a dental implant or an orthopedicimplant. In some cases, a device described herein comprises a dentalimplant. In other cases, a device described herein comprises anorthopedic implant.

In some instances, a compound described herein is coated onto an implantto prevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto a dental implant to prevent and/or reduce biofouling (e.g.,microfouling such as bacteria adhesion or biofilm). In some instances, acompound described herein is coated onto an orthopedic implant toprevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm).

In some embodiments, a device described herein comprises an IV. In someinstances, a compound described herein is coated onto an IV to preventand/or reduce biofouling (e.g., microfouling such as bacteria adhesionor biofilm).

In some embodiments, a device described herein comprises a prosthesis.In some cases, a prosthesis comprises an artificial bone, an artificialjoint, an artificial organ, or a denture. In some cases, an artificialorgan comprises an artificial pancreas, an artificial heart, anartificial limb, or a heart valve. In some embodiments, a devicedescribed herein comprises an artificial bone, an artificial joint, anartificial organ or a denture. In some embodiments, a device describedherein comprises an artificial pancreas, an artificial heart, anartificial limb, or a heart valve.

In some instances, a compound described herein is coated onto prosthesisto prevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto an artificial bone, an artificial joint, an artificialorgan, or a denture to prevent and/or reduce biofouling (e.g.,microfouling such as bacteria adhesion or biofilm). In some instances, acompound described herein is coated onto an artificial pancreas, anartificial heart, an artificial limb, or a heart valve to prevent and/orreduce biofouling (e.g., microfouling such as bacteria adhesion orbiofilm).

In some embodiments, a device described herein comprises a stent. Insome instances, a stent is a small expandable tube used to thepassageway of a blood vessel or duct remains open. In some cases, astent comprises a coronary stent, a vascular stent, or a biliary stent.In some instances, a coronary stent is also referred to as a cardiacstent or a heart stent. In some embodiments, a device described hereincomprises a coronary stent, a vascular stent, or a biliary stent.

In some instances, a compound described herein is coated onto stent toprevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto a coronary stent, a vascular stent, or a biliary stent toprevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm).

In some instances, a device described herein comprises shunt. In someinstances, a shunt is a hole or a small passage which allows fluidmovement from one part of a body to another. In some instances, a shuntdiffers from a stent in that a shunt connects two previously unconnectedportions.

In some instances, a shunt is an acquired shunt. In some cases, a shuntcomprises a cardiac shunt, a cerebral shunt, a lumbar-peritoneal shunt,a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt (PSS),a portacaval shunt, or a vesico-amniotic shunt. In some cases, a cardiacshunt comprises a right-to-left, left-to-right, or bidirectional shunt.In some cases, a cerebral shunt comprises drainage of excesscerebrospinal fluid from the brain into the chest or abdomen cavity. Insome cases, a lumbar-peritoneal shunt comprises channeling cerebrospinalfluid from the lumbar thecal sac into the peritoneal cavity. In someinstances, a peritoneovenous shunt (also referred to as Denver shunt)drains peritoneal fluid from the peritoneum into the veins. In somecases, a portosystemic shunt (PSS) is a liver shunt which allows bypassof the liver by the circulatory system. In some cases, a portacavalshunt connects the portal vein with the inferior vena cava, fortreatment of high blood pressure in the liver. In some cases, avesico-amniotic shunt is for drainage of excess fluid in a fetus bladderinto the surrounding area. In some cases, a device described hereincomprises a cardiac shunt, a cerebral shunt, a lumbar-peritoneal shunt,a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt (PSS),a portacaval shunt, or a vesico-amniotic shunt.

In some instances, a compound described herein is coated onto shunt toprevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto a cardiac shunt, a cerebral shunt, a lumbar-peritonealshunt, a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt(PSS), a portacaval shunt, or a vesico-amniotic shunt to prevent and/orreduce biofouling (e.g., microfouling such as bacteria adhesion orbiofilm).

In some instances, a device described herein comprises a scope. In somecases, a scope is a medical instrument used in an image-guided surgery.In some cases, a scope comprises endoscope or laparoscope. Endoscopy isa medical procedure for examining the GI tract with the aid of anendoscope. In some cases, endoscopy further comprises sigmoidoscopy andcolonoscopy.

Laparoscopy is a diagnostic procedure for examining internal organsutilizing a laparoscope. In some instances, a device described hereincomprises a scope used in endoscopy. In other instances, a devicedescribed herein comprises a scope used in laparoscopy.

In some instances, a compound described herein is coated onto scope toprevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto endoscope to prevent and/or reduce biofouling (e.g.,microfouling such as bacteria adhesion or biofilm). In some instances, acompound described herein is coated onto laparoscope to prevent and/orreduce biofouling (e.g., microfouling such as bacteria adhesion orbiofilm).

In some embodiments, a device described herein comprises suturingmaterial, valve, rod, tubing, wiring, electrode, clip, fastener, or acombination thereof. In some instances, a compound described herein iscoated onto suturing material, valve, rod, tubing, wiring, electrode,clip, fastener, or a combination thereof to prevent and/or reducebiofouling (e.g., microfouling such as bacteria adhesion or biofilm).

In some embodiments, a device described herein comprises a syringe. Insome cases, a syringe further comprises a needle. In some instances, acompound described herein is coated onto a syringe to prevent and/orreduce biofouling (e.g., microfouling such as bacteria adhesion orbiofilm).

In some embodiments, a device described herein comprises a container,such as for storage of one or more medical devices. In some instances, acompound described herein is coated onto a container to prevent and/orreduce biofouling (e.g., microfouling such as bacteria adhesion orbiofilm).

In some embodiments, a device described herein comprises a bandage or apatch. In some cases, a device described herein comprises a bandage. Inother cases, a device described herein comprises a patch.

In some instances, a compound described herein is coated onto a bandageto prevent and/or reduce biofouling (e.g., microfouling such as bacteriaadhesion or biofilm). In some instances, a compound described herein iscoated onto patch to prevent and/or reduce biofouling (e.g.,microfouling such as bacteria adhesion or biofilm).

In one aspect, described herein is a device coated by a compound ofFormula (I):

-   -   wherein    -   A is selected from —C(═O)—, —S(═O)—, —S(═O)₂—, and        —S(═O)(—NR³)—;    -   L is selected from —OQ, —NR³Q, and —N(R³)₂Q⁺;    -   Q is a structure represented by a formula:

-   -   Z is selected from —CR^(6a)R^(6b), —C(═O)—, —C(═NH)—, and        —C(═NH)NR⁷—;    -   m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each R³ is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄ alkyl,        optionally substituted aryl, and —X-optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(4a), R^(4b), R^(5a), R^(5c), R^(6a), and R^(6b) is        independently selected from hydrogen, halogen, —CN, —OR⁹,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted aryl, —NR^(8a)R^(8b),        —NR^(8a)R^(8b)R^(8c+), —S(═O)₂O⁻, —S(═O)₂OR⁹, —C(═O)O⁻, and        —C(═O)OR⁹;    -   R^(5b) is —OR^(10b), —NR^(10a)R^(10b), or        —NR^(10a)R^(10b)R^(10c+);    -   each R⁷, R^(8a), R^(8b), R^(8c), and R⁹ is independently        selected from hydrogen and optionally substituted C₁-C₄ alkyl,        and optionally substituted aryl;    -   each R^(10a) and R^(10c) is independently selected from        hydrogen, optionally substituted C₁-C₄ alkyl, optionally        substituted aryl, -(optionally substituted        C₁-C₈alkylene)S(═O)₂—, -(optionally substituted        C₁-C₈alkylene)S(═O)₂OH, -(optionally substituted        C₁-C₈alkylene)C(═O)O⁻, and -(optionally substituted        C₁-C₈alkylene)C(═O)OH; and    -   R^(10b) is —C(═O)—C₂-C₆alkenyl, —S(═O)—C₂-C₆alkenyl, or        —S(═O)₂—C₂-C₆alkenyl.

In some embodiments, the compound of Formula (I) is not:

-   -   N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide;    -   N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide; or    -   2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

In some embodiments, the device coated by a compound of Formula (I),comprises a residue of the compound of Formula (I). In some embodiments,the residue of a compound of Formula (I) comprises a singlet nitreneresidue.

In some embodiments, the compound of Formula (I) has a structure asdescribed above.

In some embodiments, different variables of a compound of Formula (I)are as described above.

In some embodiments, the compound of Formula (I) has a structure ofFormula (Ia), Formula (Ib), Formula (Ic), Formula (Id), Formula (Ie),Formula (If), Formula (Ig), or Formula (Ih) as described above.

In some embodiments, the compound of Formula (I) is selected fromcompounds as described above.

In another aspect, described herein is a device coated by a compound ofFormula (II):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   0<x<1; and    -   wherein the compound of Formula (II) is charged or zwitterionic.

In some embodiments, a compound of Formula (II) is not

In some embodiments, x in Formula (II) is not about 0.9434.

In some embodiments, a compound of Formula (II) is not obtained by using2 g sulfobetaine methacrylate monomer and 156 mg perfluorophenylazidemethacrylamide monomer.

In some embodiments, different variables of a compound of Formula (II)are as described above.

In another aspect, described herein is a device coated by a compound ofFormula (III):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O—, or        —C(═O)OR^(9a);    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   0<x<1.

In some embodiments, a compound of Formula (III) is charged orzwitterionic. In some embodiments, a compound of Formula (III) comprisesa positively charged repeating unit. In some embodiments a compound ofFormula (III) comprises a negatively charged repeating unit. In someembodiments, a compound of Formula (III) comprises positively chargedrepeating units and negatively charged repeating units. In someembodiments, the ratio of positively charged repeating units andnegatively charged repeating units in a compound of Formula (III) isfrom about 10:1 to about 1:10. In some embodiments, the ratio ofpositively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is from about 5:1 to about 1:5 Insome embodiments, the ratio of positively charged repeating units andnegatively charged repeating units in a compound of Formula (III) isfrom about 2:1 to about 1:2. In some embodiments, the ratio ofpositively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is about 1:1.

In some embodiments, different variables of a compound of Formula (III)are as described above.

In another aspect, described herein is a device coated by a copolymer,comprising:

a) a repeating unit of Formula (VII):

wherein

-   each R^(1a) and R^(1b) is independently selected from hydrogen and    halogen;-   each R^(2a) and R^(2b) is independently selected from halogen, —CN,    and optionally substituted C₁-C₆ fluoroalkyl;-   each A¹ and A² is independently selected from —C(═O)—, —S(═O)—,    —S(═O)₂—, and —S(═O)(═NR^(3c))—;-   each B¹ and B² is independently selected from —O— and —NR^(3c)—;-   Z¹ is —(CR^(6c)R^(6d))_(s)—;-   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is    independently selected from hydrogen, halogen, —CN, —OR^(9a),    optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄    fluoroalkyl, optionally substituted C₂-C₆ alkenyl, —NR^(3c)R^(3d),    —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(11a), R^(11b), and R^(11c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and-   s is an integer selected from 1, 2, 3, 4, and 5;    b) a repeating unit of Formula (VIII):

wherein,

-   A³ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B³ is —O— or —NR^(3c)—;-   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);-   Z² is —(CR^(6c)R^(6d))_(t)—;-   Z³ is —(CR^(6c)R^(6d))_(p);-   each R^(3a) and R^(3b) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, and optionally substituted    benzyl;-   each R^(6c) and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(12a), R^(12b), and R^(12c) is independently selected    from hydrogen, optionally substituted C₁-C₄ alkyl, and optionally    substituted aryl;-   t is an integer selected from 1, 2, 3, 4, or 5;-   p is an integer selected from 1, 2, 3, 4, or 5; and    wherein the repeating unit of Formula (VIII) is charged or    zwitterionic; and    c) a repeating unit of Formula (IX):

-   A⁴ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;-   B⁴ is —O— or —NR^(3c)—;-   Z⁴ is —(CR^(6c)R^(6d))_(k)—;-   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+) optionally    substituted C₁-C₄ alkyl, optionally substituted C₁-C₆ fluoroalkyl,    —S(═O)₂O⁻, —S(═O)₂R^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);-   each R^(6c), and R^(6d) is independently selected from hydrogen,    halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,    optionally substituted C₁-C₄ fluoroalkyl, optionally substituted    C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻,    and —C(═O)OR^(9a);-   each R^(3c) and R^(3d) is independently selected from hydrogen,    optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄    alkyl, optionally substituted C₂-C₆ alkenyl, and optionally    substituted aryl;-   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;-   each R^(9a), R^(9b), R^(9c), R^(13a), R^(13b), and R^(13c), is    independently selected from hydrogen, optionally substituted C₁-C₄    alkyl, and optionally substituted aryl; and-   k is an integer selected from 1-10.

In some embodiments, the repeating unit of Formula (IX) is charged orzwitterionic.

In some embodiments, different variables of a compound of Formula (VII),Formula (VIII), and Formula (IX) are as described above.

Biofouling-Resistant Medical Devices

In some embodiments, disclosed herein is a biofouling-resistant medicaldevice, wherein a surface of the medical device is coated with one ormore compounds of Formula (I), (II), or (III) described herein having anumber-average molecular weight of between about 10,000 and about250,000. In some embodiments, disclosed herein is a biofouling-resistantmedical device, wherein a surface of the medical device is coated withone or more copolymers comprising repeating units of Formula (VII),(VIII), and (IX) described herein having a number-average molecularweight of between about 10,000 and about 250,000.

In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of at least about 10,000, about 20,000,about 30,000, about 40,000, about 50,000, about 60,000, about 70,000,about 80,000, about 90,000, about 100,000, about 110,000, about 120,000,about 130,000, about 140,000, about 150,000, about 160,000, about170,000, about 180,000, about 190,000, or about 200,000. In someembodiments, the phenyl azide-based copolymer has a number-averagemolecular weight of no more than about 10,000, about 20,000, about30,000, about 40,000, about 50,000, about 60,000, about 70,000, about80,000, about 90,000, about 100,000, about 110,000, about 120,000, about130,000, about 140,000, about 150,000, about 160,000, about 170,000,about 180,000, about 190,000, or about 200,000.

In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about20,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about40,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about60,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about80,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about100,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about120,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about140,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 10,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about40,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about60,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about80,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about100,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about120,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about140,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about60,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about80,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about100,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about120,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about140,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 40,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 60,000 and about80,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 60,000 and about100,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 60,000 and about120,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 60,000 and about140,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 60,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 60,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 60,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 80,000 and about100,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 80,000 and about120,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 80,000 and about140,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 80,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 80,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 80,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 100,000 and about120,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 100,000 and about140,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 100,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 100,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 100,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 120,000 and about140,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 120,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 120,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 120,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 140,000 and about160,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 140,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 140,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 160,000 and about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 160,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 200,000 and about250,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of about 10,000. In some embodiments,the phenyl azide-based copolymer has a number-average molecular weightof about 20,000. In some embodiments, the phenyl azide-based copolymerhas a number-average molecular weight of about 40,000. In someembodiments, the phenyl azide-based copolymer has a number-averagemolecular weight of about 60,000. In some embodiments, the phenylazide-based copolymer has a number-average molecular weight of about80,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of about 100,000. In some embodiments,the phenyl azide-based copolymer has a number-average molecular weightof about 120,000. In some embodiments, the phenyl azide-based copolymerhas a number-average molecular weight of about 140,000. In someembodiments, the phenyl azide-based copolymer has a number-averagemolecular weight of about 160,000. In some embodiments, the phenylazide-based copolymer has a number-average molecular weight of about200,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of about 250,000.

In some embodiments, disclosed herein is a biofouling-resistant medicaldevice, wherein a surface of the medical device is coated with one ormore compounds of Formula (I), (II), or (III) described herein having anumber-average molecular weight of between about 14,000 and about21,000. In some embodiments, disclosed herein is a biofouling-resistantmedical device, wherein a surface of the medical device is coated withone or more copolymers comprising repeating units of Formula (VII),(VIII), and (IX) described herein having a number-average molecularweight of between about 14,000 and about 21,000.

In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 14,000 and about15,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 14,000 and about16,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 14,000 and about17,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 14,000 and about18,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 14,000 and about19,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 14,000 and about20,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 15,000 and about16,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 15,000 and about17,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 15,000 and about18,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 15,000 and about19,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 15,000 and about20,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 15,000 and about21,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 16,000 and about17,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 16,000 and about18,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 16,000 and about19,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 16,000 and about20,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 16,000 and about21,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 17,000 and about18,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 17,000 and about19,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 17,000 and about20,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 17,000 and about21,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 18,000 and about19,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 18,000 and about20,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 18,000 and about21,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 19,000 and about20,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 19,000 and about21,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of between about 20,000 and about21,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of about 14,000. In some embodiments,the phenyl azide-based copolymer has a number-average molecular weightof about 15,000. In some embodiments, the phenyl azide-based copolymerhas a number-average molecular weight of about 16,000. In someembodiments, the phenyl azide-based copolymer has a number-averagemolecular weight of about 17,000. In some embodiments, the phenylazide-based copolymer has a number-average molecular weight of about18,000. In some embodiments, the phenyl azide-based copolymer has anumber-average molecular weight of about 19,000. In some embodiments,the phenyl azide-based copolymer has a number-average molecular weightof about 20,000. In some embodiments, the phenyl azide-based copolymerhas a number-average molecular weight of about 21,000.

In some embodiments, disclosed herein is a biofouling-resistant medicaldevice, wherein a surface of the medical device is coated with one ormore compounds of Formula (I), (II), or (III) described herein having apolydispersity index (PDI) of between about 1 and 1.5. In someembodiments, disclosed herein is a biofouling-resistant medical device,wherein a surface of the medical device is coated with one or morecopolymers comprising repeating units of Formula (VII), (VIII), and (IX)described herein having a polydispersity index (PDI) of between about 1and 1.5.

In some embodiments, the surface of the medical device is coated with aphenyl azide-based copolymer having a polydispersity index (PDI) of atleast about 1, about 1.1, about 1.2, about 1.3, about 1.4, or about 1.5.In some embodiments, the surface of the medical device is coated with aphenyl azide-based copolymer having a polydispersity index (PDI) of nomore than about 1, about 1.1, about 1.2, about 1.3, about 1.4, or about1.5.

In some embodiments, the surface of the medical device is coated with aphenyl azide-based copolymer having a polydispersity index (PDI) ofbetween about 1 and 1.1. In some embodiments, the surface of the medicaldevice is coated with a phenyl azide-based copolymer having apolydispersity index (PDI) of between about 1 and 1.2. In someembodiments, the surface of the medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of betweenabout 1 and 1.3. In some embodiments, the surface of the medical deviceis coated with a phenyl azide-based copolymer having a polydispersityindex (PDI) of between about 1 and 1.4. In some embodiments, the surfaceof the medical device is coated with a phenyl azide-based copolymerhaving a polydispersity index (PDI) of between about 1 and 1.5. In someembodiments, the surface of the medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of betweenabout 1.1 and 1.2. In some embodiments, the surface of the medicaldevice is coated with a phenyl azide-based copolymer having apolydispersity index (PDI) of between about 1.1 and 1.3. In someembodiments, the surface of the medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of betweenabout 1.1 and 1.4. In some embodiments, the surface of the medicaldevice is coated with a phenyl azide-based copolymer having apolydispersity index (PDI) of between about 1.1 and 1.5. In someembodiments, the surface of the medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of betweenabout 1.2 and 1.3. In some embodiments, the surface of the medicaldevice is coated with a phenyl azide-based copolymer having apolydispersity index (PDI) of between about 1.2 and 1.4. In someembodiments, the surface of the medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of betweenabout 1.2 and 1.5. In some embodiments, the surface of the medicaldevice is coated with a phenyl azide-based copolymer having apolydispersity index (PDI) of between about 1.3 and 1.4. In someembodiments, the surface of the medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of betweenabout 1.3 and 1.5. In some embodiments, the surface of the medicaldevice is coated with a phenyl azide-based copolymer having apolydispersity index (PDI) of between about 1.4 and 1.5. In someembodiments, the PDI is about 1. In some embodiments, the PDI is about1.1. In some embodiments, the PDI is about 1.2. In some embodiments, thePDI is about 1.3. In some embodiments, the PDI is about 1.4. In someembodiments, the PDI is about 1.5. In some embodiments, the PDI is about1.11. In some embodiments, the PDI is about 1.12. In some embodiments,the PDI is about 1.13. In some embodiments, the PDI is about 1.14. Insome embodiments, the PDI is about 1.15. In some embodiments, the PDI isabout 1.16. In some embodiments, the PDI is about 1.17. In someembodiments, the PDI is about 1.18. In some embodiments, the PDI isabout 1.19. In some embodiments, the PDI is about 1.21. In someembodiments, the PDI is about 1.22. In some embodiments, the PDI isabout 1.23. In some embodiments, the PDI is about 1.24. In someembodiments, the PDI is about 1.25.

In some embodiments, the medical device comprises a dental instrument ora medical instrument. In some embodiments, the medical device comprisesan implant, an IV, a prosthesis, a suturing material, a valve, a stent,a catheter, a rod, a shunt, a scope, a contact lens, a tubing, a wiring,an electrode, a clip, a fastener, a syringe, a container, or acombination thereof. In some embodiments, the medical device is acontact lens. In some embodiments, the medical device is a catheter. Insome embodiments, the catheter is an indwelling catheter. In someembodiments, the catheter comprises a uretic catheter or a Foleycatheter. In some embodiments, the medical device is a scope. In someembodiments, the scope comprises a scope utilized in an image-guidedsurgery. In some embodiments, the scope comprises a scope utilized inendoscopy or laparoscopy.

In some embodiments, the medical device comprises auditory prostheses,artificial larynx, dental implants, mammary implants, penile implants,cranio/facial tendons, tendons, ligaments, menisci, or disks. In someembodiments, the medical device comprises artificial bones, artificialjoints, or artificial organs. In some embodiments, the artificial organscomprise artificial pancreas, artificial hearts, artificial limbs, orheart valves. In some embodiments, the medical device comprises abandage or a patch.

In some embodiments, the copolymer comprises zwitterionic copolymer. Insome embodiments, the zwitterionic copolymer comprises polysulfobetaine.

In some embodiments, the biofouling is produced by a bacterium, a virus,and/or a fungus.

Non-Medical Devices

In some embodiments, a device described herein comprises a non-medicaldevice. In some instances, a non-medical device comprises a marinevessel or an underwater construction. In some cases, a surface of anon-medical device for coating a compound described herein comprises asurface that is immersed in water. In some cases, the immersion is animmersion of at least 30 minutes, 1 hour, 6 hours, 12 hours, 1 day, 2days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days,11 days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2 months,3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 10months, 11 months, 1 year, 2 years, 3 years, 4 years, 5 years, 10 years,or more.

In some instances, a device described herein comprises a marine vessel.In some instances, a surface of a marine vessel comprises a surface thatis immersed in water. In some cases, a surface of a marine vesselcomprises a surface that is immersed in water for at least 30 minutes, 1hour, 6 hours, 12 hours, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days,7 days, 8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days, 15days, 30 days, 1 month, 2 months, 3 months, 4 months, 5 months, 6months, 7 months, 8 months, 9 months, 10 months, 11 months, 1 year, 2years, 3 years, 4 years, 5 years, 10 years, or more. In some instances,the surface of a device for coating a compound described hereincomprises the hull of a marine vessel.

In some instances, a device described herein comprises an underwaterconstruction. In some instances, an underwater construction comprises anunderwater cable, a current measurement instrument, or an offshore oilplatform. In some cases, a device described herein comprises anunderwater cable. In some cases, a device described herein comprises acurrent measurement instrument. In other cases, a device describedherein comprises an offshore oil platform.

In some cases, an underwater construction is a construction in which theconstruction is immersed in water for at least 30 minutes, 1 hour, 6hours, 12 hours, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days,8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days, 15 days, 30days, 1 month, 2 months, 3 months, 4 months, 5 months, 6 months, 7months, 8 months, 9 months, 10 months, 11 months, 1 year, 2 years, 3years, 4 years, 5 years, or more. In some cases, a surface of anunderwater construction is a construction in which the surface isimmersed in water for at least 30 minutes, 1 hour, 6 hours, 12 hours, 1day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10days, 11 days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2months, 3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9months, 10 months, 11 months, 1 year, 2 years, 3 years, 4 years, 5years, 10 years, or more. In some instances, a device described hereincomprises an underwater construction in which the surface is immersed inwater for at least 30 minutes, 1 hour, 6 hours, 12 hours, 1 day, 2 days,3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days, 11days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2 months, 3months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 10months, 11 months, 1 year, 2 years, 3 years, 4 years, 5 years, 10 years,or more.

In some embodiments, a compound described herein is coated onto a device(e.g., a medical device or a non-medical device). In some cases, acompound described herein is coated directly onto a device (e.g., amedical device or a non-medical device). In other instances, a compounddescribed herein is coated indirectly onto a device (e.g., a medicaldevice or a non-medical device). In some cases, the coating comprisesdip-coating. In other cases, the coating comprises spray coating.

In some embodiments, a compound described herein is coated onto a device(e.g., a medical device or a non-medical device) to reduce the formationof biofouling. In some cases, the formation of biofouling is reduced byabout 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%,99.9%, or more relative to a device not coated with the compound. Insome instances, the formation of biofouling is reduced by about 10%, ormore relative to a device not coated with the compound. In someinstances, the formation of biofouling is reduced by about 20%, or morerelative to a device not coated with the compound. In some instances,the formation of biofouling is reduced by about 30%, or more relative toa device not coated with the compound. In some instances, the formationof biofouling is reduced by about 40%, or more relative to a device notcoated with the compound. In some instances, the formation of biofoulingis reduced by about 50%, or more relative to a device not coated withthe compound. In some instances, the formation of biofouling is reducedby about 60%, or more relative to a device not coated with the compound.In some instances, the formation of biofouling is reduced by about 70%,or more relative to a device not coated with the compound. In someinstances, the formation of biofouling is reduced by about 80%, or morerelative to a device not coated with the compound. In some instances,the formation of biofouling is reduced by about 90%, or more relative toa device not coated with the compound. In some instances, the formationof biofouling is reduced by about 95%, or more relative to a device notcoated with the compound. In some instances, the formation of biofoulingis reduced by about 99%, or more relative to a device not coated withthe compound. In some instances, the formation of biofouling is reducedby about 99.5%, or more relative to a device not coated with thecompound. In some instances, the formation of biofouling is reduced byabout 99.9%, or more relative to a device not coated with the compound.

IV. Methods of Making

In a further aspect, described herein is a method of preparing abiofouling-resistant device, comprising:

-   -   a) contacting a surface of a device with a mixture (e.g., a        solution) comprising a copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        copolymer onto the surface of the device, thereby making the        biofouling-resistant device;    -   wherein the copolymer comprises a phenyl azide-based copolymer;        and wherein the copolymer has a number-average molecular weight        of between about 10,000 and about 250,000.

In some embodiments, also described herein is a method of preparing acopolymer modified biofouling-resistant silicon-based device comprising:

-   -   a) contacting a surface of a silicon-based device with a mixture        (e.g., a solution) comprising a charged or zwitterion copolymer;        and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        copolymer onto the surface of the silicon-based device, thereby        generating the charged or zwitterion copolymer modified device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer.

In some embodiments, also described herein is a method of preparing acharged or zwitterion copolymer modified biofouling-resistant devicecomprising:

-   -   a) contacting a surface of a device with a mixture (e.g., a        solution) comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        copolymer onto the surface of the device, thereby generating the        charged or zwitterion copolymer modified device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        10,000 and about 250,000.

In some embodiments, the method comprises one-step grafting reactionthat modifies the surface of a device.

In some embodiments, the device is a medical device described herein. Insome embodiments, the device is a non-medical device described herein.

In some embodiments, the time sufficient to undergo photografting is atleast 1 minute, at least 2 minutes, 3 minutes, 4 minutes, 5 minutes, 6minutes, 7 minutes, 8 minutes, 9 minutes, 10 minutes, 15 minutes, 20minutes, 25 minutes or 30 minutes.

In some embodiments, the light source is an ultraviolet light source. Insome embodiments, the ultraviolet light source has an intensity of atleast 500 μW/cm². In some embodiments, the ultraviolet light source hasan intensity of at least 600 μW/cm². In some embodiments, theultraviolet light source has an intensity of at least 700 μW/cm². Insome embodiments, the ultraviolet light source has an intensity of atleast 800 μW/cm². In some embodiments, the ultraviolet light source hasan intensity of at least 900 μW/cm². In some embodiments, theultraviolet light source has an intensity of at least 1000 μW/cm².

In some embodiments, the ultraviolet light source has a wavelength ofbetween 240 nm and 280 nm, between 240 nm and 275 nm, between 240 nm and270 nm, between 240 nm and 265 nm, between 240 nm and 260 nm, between240 nm and 255 nm, between 240 nm and 250 nm, between 240 nm and 245 nm,between 250 nm and 280 nm, between 250 nm and 275 nm, between 250 nm and270 nm, between 250 nm and 265 nm, between 250 nm and 260 nm, between255 nm and 280 nm, between 255 nm and 275 nm, between 255 nm and 270 nm,between 255 nm and 265 nm, between 255 nm and 260 nm, between 260 nm and280 nm, between 260 nm and 275 nm, between 260 nm and 270 nm, or between270 nm and 280 nm.

In some embodiments, the ultraviolet light source has a wavelength of atleast 240 nm, 245 nm, 250 nm, 251 nm, 252 nm, 253 nm, 254 nm, 255 nm,256 nm, 257 nm, 258 nm, 259 nm, 260 nm, 261 nm, 262 nm, 263 nm, 264 nm,265 nm, 266 nm, 267 nm, 268 nm, 269 nm, 270 nm, 275 nm or 280 nm. Insome embodiments, the ultraviolet light source has a wavelength of nomore than 240 nm, 245 nm, 250 nm, 251 nm, 252 nm, 253 nm, 254 nm, 255nm, 256 nm, 257 nm, 258 nm, 259 nm, 260 nm, 261 nm, 262 nm, 263 nm, 264nm, 265 nm, 266 nm, 267 nm, 268 nm, 269 nm, 270 nm, 275 nm or 280 nm.

In a further aspect, described herein is a method of preparing abiofouling-resistant device, comprising:

-   -   a) contacting a surface of a device with a mixture (e.g., a        solution) comprising a copolymer; and    -   b) treating the surface of the device of step a) with a heat        source for a time sufficient to undergo thermografting of the        copolymer onto the surface of the device, thereby making the        biofouling-resistant device;    -   wherein the copolymer comprises a phenyl azide-based copolymer;        and wherein the copolymer has a number-average molecular weight        of between about 10,000 and about 250,000.

In some embodiments, also described herein is a method of preparing acopolymer modified biofouling-resistant silicon-based device comprising:

-   -   a) contacting a surface of a silicon-based device with a mixture        (e.g., a solution) comprising a charged or zwitterion copolymer;        and    -   b) treating the surface of the device of step a) with a heat        source for a time sufficient to undergo thermografting of the        copolymer onto the surface of the silicon-based device, thereby        generating the charged or zwitterion copolymer modified device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer.

In some embodiments, also described herein is a method of preparing acharged or zwitterion copolymer modified biofouling-resistant devicecomprising:

-   -   a) contacting a surface of a device with a mixture (e.g., a        solution) comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a heat        source for a time sufficient to undergo thermografting of the        copolymer onto the surface of the device, thereby generating the        charged or zwitterion copolymer modified device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer has a number-average molecular weight of between about        10,000 and about 250,000.

In some embodiments, the method comprises one-step grafting reactionthat modifies the surface of a device.

In some embodiments, the device is a medical device described herein. Insome embodiments, the device is a non-medical device described herein.

In some embodiments, the time sufficient to undergo thermografting is 1minute, 2 minutes, 3 minutes, 4 minutes, 5 minutes, 6 minutes, 7minutes, 8 minutes, 9 minutes, 10 minutes, 15 minutes, 20 minutes, 25minutes, 30 minutes, 45 minutes, 1 hour, 1.5 hours, 2 hours, 3 hours, 4hours, 5 hours, 6 hours, 9 hours, 12 hours, 18 hours, or 24 hours. Insome embodiments, the time sufficient to undergo thermografting is atleast 1 minute, at least 2 minutes, at least 3 minutes, at least 4minutes, at least 5 minutes, at least 6 minutes, at least 7 minutes, atleast 8 minutes, at least 9 minutes, at least 10 minutes, at least 15minutes, at least 20 minutes, at least 25 minutes, at least 30 minutes,at least 45 minutes, at least 1 hour, at least 1.5 hours, at least 2hours, at least 3 hours, at least 4 hours, at least 5 hours, at least 6hours, at least 9 hours, at least 12 hours, or at least 18 hours. Insome embodiments, the time sufficient to undergo thermografting is atmost 2 minutes, at most 3 minutes, at most 4 minutes, at most 5 minutes,at most 6 minutes, at most 7 minutes, at most 8 minutes, at most 9minutes, at most 10 minutes, at most 15 minutes, at most 20 minutes, atmost 25 minutes, at most 30 minutes, at most 45 minutes, at most 1 hour,at most 1.5 hours, at most 2 hours, at most 3 hours, at most 4 hours, atmost 5 hours, at most 6 hours, at most 9 hours, at most 12 hours, atmost 18 hours, or at most 24 hours.

In some embodiments, the heat source provides a grafting temperaturebetween 40 and 380 degree Celsius (° C.). In some embodiments, the heatsource provides a grafting temperature between 40° C. and 360° C. Insome embodiments, the heat source provides a grafting temperaturebetween 60° C. and 320° C. In some embodiments, the heat source providesa grafting temperature between 80° C. and 260° C. In some embodiments,the heat source provides a grafting temperature between 100° C. and 220°C. In some embodiments, the heat source provides a grafting temperaturebetween 120° C. and 220° C. In some embodiments, the heat sourceprovides a grafting temperature between 40° C. and 60° C., between 60°C. and 80° C., between 80° C. and 100° C., between 100° C. and 120° C.,between 120° C. and 140° C., between 140° C. and 160° C., between 160°C. and 180° C., between 180° C. and 200° C., between 200° C. and 220°C., between 220° C. and 240° C., between 240° C. and 260° C., between260° C. and 280° C., between 280° C. and 300° C., between 300° C. and320° C., between 320° C. and 340° C., or between 340° C. and 360° C. Insome embodiments, the heat source provides a grafting temperaturebetween 60° C. and 80° C., between 80° C. and 100° C., between 100° C.and 120° C., between 120° C. and 140° C., between 140° C. and 160° C.,between 160° C. and 180° C., between 180° C. and 200° C., between 200°C. and 220° C., or between 220° C. and 240° C. In some embodiments, theheat source provides a grafting temperature of 60° C., 80° C., 100° C.,120° C., 140° C., 160° C., 180° C., 200° C., 220° C., 240° C., 260° C.,280° C., or 300° C. In some embodiments, the heat source provides agrafting temperature of 60° C., 80° C., 100° C., 120° C., 140° C., 160°C., 180° C., 200° C., or 220° C. In some embodiments, the heat sourceprovides a grafting temperature of at least 60° C., at least 80° C., atleast 100° C., at least 120° C., at least 140° C., at least 160° C., atleast 180° C., at least 200° C., at least 220° C., at least 240° C., atleast 260° C., or at least 280° C. In some embodiments, the heat sourceprovides a grafting temperature of at most 80° C., at most 100° C., atmost 120° C., at most 140° C., at most 160° C., at most 180° C., at most200° C., at most 220° C., at most 240° C., at most 260° C., at most 280°C., or at most 300° C.

In some embodiments, the mixture of step a) is an aqueous solution, anaqueous colloid, or an aqueous suspension. In some embodiments, themixture of step a) is a non-aqueous solution, an aqueous colloid, or anaqueous suspension.

In some embodiments, the phenyl azide-based copolymer is a compound ofFormula (II) or (III) described herein.

In some embodiments, the mixture comprising a charged or zwitterioncopolymer has a concentration of the charged or zwitterion copolymer inthe mixture between 1 mg/mL and 30 mg/mL.

In some embodiments, the concentration of the charged or zwitterioncopolymer in the mixture is between 0.1 mg/mL and 100 mg/mL, 0.5 mg/mLand 50 mg/mL, 1 mg/mL and 25 mg/mL, between 1 mg/mL and 20 mg/mL,between 1 mg/mL and 15 mg/mL, between 1 mg/mL and 10 mg/mL, between 1mg/mL and 5 mg/mL, between 5 mg/mL and 30 mg/mL, between 5 mg/mL and 25mg/mL, between 5 mg/mL and 20 mg/mL, between 5 mg/mL and 15 mg/mL,between 5 mg/mL and 10 mg/mL, between 10 mg/mL and 30 mg/mL, between 10mg/mL and 25 mg/mL, between 10 mg/mL and 20 mg/mL, between 10 mg/mL and15 mg/mL, between 15 mg/mL and 30 mg/mL, between 15 mg/mL and 25 mg/mL,between 15 mg/mL and 20 mg/mL, between 20 mg/mL and 30 mg/mL, or between20 mg/mL and 25 mg/mL. In some embodiments, the concentration of thecharged or zwitterion copolymer in the mixture is between 25 mg/mL and30 mg/mL, between 30 mg/mL and 35 mg/mL, between 35 mg/mL and 40 mg/mL,between 40 mg/mL and 45 mg/mL, between 45 mg/mL and 50 mg/mL, between 50mg/mL and 55 mg/mL, between 55 mg/mL and 60 mg/mL, between 60 mg/mL and65 mg/mL, between 65 mg/mL and 70 mg/mL, between 70 mg/mL and 75 mg/mL,between 75 mg/mL and 80 mg/mL, between 80 mg/mL and 85 mg/mL, between 85mg/mL and 90 mg/mL, between 90 mg/mL and 95 mg/mL, or between 95 mg/mLand 100 mg/mL.

In some embodiments, the concentration of the charged or zwitterioncopolymer in the mixture is about 1 mg/mL, 2 mg/mL, 3 mg/mL, 4 mg/mL, 5mg/mL, 6 mg/mL, 7 mg/mL, 8 mg/mL, 9 mg/mL, 10 mg/mL, 11 mg/mL, 12 mg/mL,13 mg/mL, 14 mg/mL, 15 mg/mL, 16 mg/mL, 17 mg/mL, 18 mg/mL, 19 mg/mL, 20mg/mL, 21 mg/mL, 22 mg/mL, 23 mg/mL, 24 mg/mL, 25 mg/mL, 26 mg/mL, 27mg/mL, 28 mg/mL, 29 mg/mL, or 30 mg/mL. In some embodiments, theconcentration of the charged or zwitterion copolymer in the mixture isabout 31 mg/mL, 32 mg/mL, 33 mg/mL, 34 mg/mL, 35 mg/mL, 36 mg/mL, 37mg/mL, 38 mg/mL, 39 mg/mL, 40 mg/mL, 41 mg/mL, 42 mg/mL, 43 mg/mL, 44mg/mL, 45 mg/mL, 46 mg/mL, 47 mg/mL, 48 mg/mL, 49 mg/mL, 50 mg/mL, 51mg/mL, 52 mg/mL, 53 mg/mL, 54 mg/mL, 55 mg/mL, 56 mg/mL, 57 mg/mL, 58mg/mL, 59 mg/mL, or 60 mg/mL.

In some embodiments, the concentration of the charged or zwitterioncopolymer is between 0.01 to 10 mg per square centimeter of the device.In some embodiments, the concentration of the charged or zwitterioncopolymer is between 0.1 to 1 mg per square centimeter of the device. Insome embodiments, the concentration of the charged or zwitterioncopolymer is between 0.01 to 0.05, between 0.1 to 0.2, between 0.2 to0.3, between 0.3 to 0.4, between 0.4 to 0.5, between 0.5 to 0.6, between0.6 to 0.7, between 0.7 to 0.8, between 0.8 to 0.9, between 0.9 to 1,between 1 to 2, between 2 to 2, between 3 to 2, between 4 to 2, between5 to 2, between 6 to 2, between 7 to 2, between 8 to 2, or between 9 to10 per square centimeter of the device.

In some embodiments, the device comprises a polymer-based device. Insome embodiments, the polymer-based device comprises a polyolefinicdevice. In some embodiments, the polyolefinic device comprises a devicemodified with polyethylene (PE), polypropylene (PP), polyamide (PA),polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVdF),polyvinyl chloride (PVC), or a combination thereof. In some embodiments,the device comprises a microporous device or a nonwoven device. In someembodiments, the device comprises a carbon-based device comprising amoiety capable of binding with a compound that has a structure ofFormula (I), (II), or (III). In some embodiments, the device comprises acarbon-based device comprising a moiety capable of binding with acopolymer comprising a repeating unit of Formula (VII), (VIII), and(IX). In some embodiments, the carbon-based device comprises a polymermoiety. In some embodiments, the carbon-based device comprises acarbon-based polymer. In some embodiments, the carbon-based devicecomprises a polyolefin moiety. In some embodiments, the polyolefinmoiety comprises a polyethylene (PE) moiety, a polypropylene (PP)moiety, a polyamide (PA) moiety, a polytetrafluoroethylene (PTFE)moiety, a polyvinylidene fluoride (PVdF) moiety, or a polyvinyl chloride(PVC) moiety.

In some embodiments, the device comprises a carbon-based device. In someembodiments, the carbon-based device comprises a carbon-based polymer.In some embodiments, the carbon-based device comprises a polyolefinmoiety. In some embodiments, the polyolefin moiety comprisespolyethylene moiety, polypropylene moiety, polyvinyl chloride moiety,polyvinylidene fluoride moiety, polytetrafluoroethylene moiety,polychlorotrifluoroethylene moiety, or polystyrene moiety. In someembodiments, the carbon-based polymer comprises polyamide moiety,polyurethane moiety, phenol-formaldehyde resin moiety, polycarbonatemoiety, polychloroprene moiety, polyacrylonitrile moiety, polyimidemoiety, or polyester moiety. In some embodiments, the carbon-basedpolymer comprises nylon. In some embodiments, the carbon-based polymercomprises polyethylene terephthalate.

In some embodiments, the device comprises a silicon-based device. Insome embodiments, the silicon-based device comprises a silicon-basedpolymer moiety. In some embodiments, the device comprises asilicon-based device comprising a moiety capable of binding with acompound that has a structure of Formula (I), (II), or (III). In someembodiments, the device comprises a silicon-based device comprising amoiety capable of binding with a copolymer comprising a repeating unitof Formula (VII), (VIII), and (IX). In some embodiments, thesilicon-based device comprises a polymer moiety. In some embodiments,the silicon-based device comprises a siloxane polymer moiety, asesquisiloxane polymer moiety, a siloxane-silarylene polymer moiety, asilalkylene polymer moiety, a polysilane moiety, a polysilylene moiety,or a polysilazane moiety.

In some embodiments, the silicon-based device comprises a siloxanepolymer moiety. In some embodiments, the silicon-based device comprisessilicone polymer.

In some embodiments, the device comprises a carbon-based device or asilicon-based device.

In some embodiments, the copolymer comprises zwitterionic copolymer. Insome embodiments, the zwitterionic copolymer comprises polysulfobetaine.

In some embodiments, the biofouling of the biofouling-resistant medicaldevice described herein is produced by a bacterium, a virus, and/or afungus.

V. Methods of Synthesis

Methods provided by the present disclosure also include methods ofsynthesizing a compound of Formula (II) comprising: reacting a compoundof Formula (IV) or a salt or solvate thereof with a compound of Formula(V):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OH,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   0<x<1; and    -   wherein the compounds of Formula (II) and Formula (V) are each        charged or zwitterionic.

In some embodiments, a compound of Formula (II) is not

In some embodiments, x in Formula (II) is not about 0.9434.

In some embodiments, a compound of Formula (II) is not obtained by using2 g sulfobetaine methacrylate monomer and 156 mg perfluorophenylazidemethacrylamide monomer.

In some embodiments, different variables of a compound of Formula (II)are as described above.

In some embodiments, the compound of Formula (IV) has the structure of:

In some embodiments, the compound of Formula (V) has the structure of:

Methods provided by the present disclosure also include methods ofsynthesizing a compound of Formula (III) comprising: reacting a compoundof Formula (IV) or a salt or solvate thereof with a compound of Formula(VI):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+)        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a);    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   0<x<1.

In some embodiments, the compounds of Formula (III) and Formula (VI)each charged or zwitterionic. In some embodiments, a compound of Formula(VI) comprises a positively charged compound of Formula (VI). In someembodiments a compound of Formula (VI) comprises a negatively chargedcompound of Formula (VI). In some embodiments, a compound of Formula(III) comprises positively charged repeating units. In some embodimentsa compound of Formula (III) comprises negatively charged repeatingunits. In some embodiments, a compound of Formula (III) comprisespositively charged repeating units and negatively charged repeatingunits. In some embodiments, the ratio of positively charged repeatingunits and negatively charged repeating units in a compound of Formula(III) is from about 10:1 to about 1:10. In some embodiments, the ratioof positively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is from about 5:1 to about 1:5 Insome embodiments, the ratio of positively charged repeating units andnegatively charged repeating units in a compound of Formula (III) isfrom about 2:1 to about 1:2. In some embodiments, the ratio ofpositively charged repeating units and negatively charged repeatingunits in a compound of Formula (III) is about 1:1.

In some embodiments, different variables of a compound of Formula (III)are as described above.

In some embodiments, the compound of Formula (IV) has the structure of:

In some embodiments, the compound of Formula (VI) has the structure of:

In some embodiments, the compound of Formula (VI) has the structure of:

Any combination of the groups described above or below for the variousvariables is contemplated herein. Throughout the specification, groupsand substituents thereof are chosen by one skilled in the field toprovide stable moieties and compounds.

Properties of Biofouling-Resistant Coatings

In some embodiments, biofouling-resistant coatings disclosed herein havevarious properties that provide the superior function of the devices,including excellent flux, improved hydrophilicity, improved resistanceto fouling, tunable surface charge properties, higher thermal stability,higher chemical stability, higher solvent stability, or a combinationthereof. It is also understood that the coatings disclosed herein haveother properties.

In some embodiments, a biofouling-resistant coating disclosed herein hasa water receding angle of less than about 70°. In some embodiments, abiofouling-resistant coating disclosed herein has a water receding angleof less than about 65°. In some embodiments, a biofouling-resistantcoating disclosed herein has a water receding angle of less than about60°. In some embodiments, a biofouling-resistant coating disclosedherein has a water receding angle of less than about 55°. In someembodiments, a biofouling-resistant coating disclosed herein has a waterreceding angle of less than about 50°. In some embodiments, abiofouling-resistant coating disclosed herein has a water receding angleof less than about 45°. In some embodiments, a biofouling-resistantcoating disclosed herein has a water receding angle of less than about40°. In some embodiments, a biofouling-resistant coating disclosedherein has a water receding angle of less than about 35°. In someembodiments, a biofouling-resistant coating disclosed herein has a waterreceding angle of less than about 30°. In some embodiments, abiofouling-resistant coating disclosed herein has a water receding angleof less than about 25°. In some embodiments, a biofouling-resistantcoating disclosed herein has a water receding angle of less than about20°. In some embodiments, a biofouling-resistant coating disclosedherein has a water receding angle of less than about 15°. In someembodiments, a biofouling-resistant coating disclosed herein has a waterreceding angle of less than about 10°. In some embodiments, abiofouling-resistant coating disclosed herein has a water receding angleof less than about 5°. In some embodiments, a biofouling-resistantcoating disclosed herein has a water receding angle of about 0°. Incertain embodiments, the devices provided herein, coated by one or morebiofouling-resistant coatings described herein have a high resistance offouling.

In a further aspect, a biofouling-resistant coating disclosed hereinexhibits an improvement in at least one property selected fromresistance to fouling, hydrophilicity, surface charge, salt rejection,and roughness. In some embodiments, a biofouling-resistant coatingdisclosed herein demonstrates an improvement in at least one propertyselected from resistance to fouling, salt rejection, and hydrophilicity.In some embodiments, a biofouling-resistant coating disclosed hereindemonstrates an improvement in resistance to fouling. In someembodiments, a biofouling-resistant coating disclosed hereindemonstrates an improvement in hydrophilicity. In some embodiments, abiofouling-resistant coating disclosed herein demonstrates animprovement in surface charge. In some embodiments, abiofouling-resistant coating disclosed herein demonstrates animprovement in roughness. In some embodiments, a biofouling-resistantcoating disclosed herein demonstrates reduced surface roughness. In someembodiments, a biofouling-resistant coating disclosed hereindemonstrates an improvement in salt rejection.

In some embodiments, a biofouling-resistant coating disclosed hereincomprising one or more compounds of Formula (I), (II), or (III)described herein prevents and/or reduces biofouling. In someembodiments, a biofouling-resistant coating disclosed herein comprisingone or more copolymers comprising repeating units of Formula (VII),(VIII), and (IX) described herein prevents and/or reduces biofouling. Insome instances, biofouling comprises microfouling or macrofouling.Microfouling comprises formation of microorganism adhesion (e.g.,bacteria adhesion) and/or biofilm. Biofilm is a group of microorganismwhich adheres to a surface. In some instances, the adheredmicroorganisms are further embedded in a self-produced matrix ofextracellular polymeric substance, which comprises a polymericconglomeration of extracellular DNA, protein, and polysaccharides.Macrofouling comprises attachment of larger organism. In some instancesa biofouling-resistant coating disclosed herein prevents and/or reducesmicrofouling. In some instances, a biofouling-resistant coatingdisclosed herein prevents and/or reduces bacterial adhesion. In someinstances, a biofouling-resistant coating disclosed herein preventsand/or reduces biofilm. In other instances, a biofouling-resistantcoating disclosed herein prevents and/or reduces macrofouling.

Microfouling

In some instances, microfouling is formed by bacteria or fungi. In someinstances, microfouling is formed by bacteria. In some instances, abacterium is a gram-positive bacterium or a gram-negative bacterium. Insome cases, a bacterium is a marine bacterium.

In some cases, microfouling is formed by a gram-positive bacterium.Exemplary gram-positive bacteria include, but are not limited to,bacteria from the genus Actinomyces, Arthrobacter, Bacillus,Clostridium, Corynebacterium, Enterococcus, Lactococcus, Listeria,Micrococcus, Mycobacterium, Staphylococcus, or Streptococcus. In someinstances, a gram-positive bacterium comprises Actinomyces spp.,Arthrobacter spp., Bacillus licheniformis, Clostridium difficile,Clostridium spp., Corynebacterium spp., Enterococcus faecalis,Lactococcus spp., Listeria monocytogenes, Micrococcus spp.,Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis,Streptococcus pneumoniae, or Streptococcus pyogenes.

In some instances, microfouling is formed by a gram-positive bacteriumfrom the genus Actinomyces, Arthrobacter, Bacillus, Clostridium,Corynebacterium, Enterococcus, Lactococcus, Listeria, Micrococcus,Mycobacterium, Staphylococcus, or Streptococcus. In some instances,microfouling is formed by a gram-positive bacterium: Actinomyces spp.,Arthrobacter spp., Bacillus licheniformis, Clostridium difficile,Clostridium spp., Corynebacterium spp., Enterococcus faecalis,Lactococcus spp., Listeria monocytogenes, Micrococcus spp.,Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis,Streptococcus pneumoniae, or Streptococcus pyogenes.

In some instances, a biofouling-resistant coating disclosed herein isresistant to fouling. In some instances, a biofouling-resistant coatingdisclosed herein prevents and/or reduces microfouling on one or more ofits surfaces. In some cases, a biofouling-resistant coating disclosedherein prevents and/or reduces microfouling formed by a gram-positivebacterium from the genus Actinomyces, Arthrobacter, Bacillus,Clostridium, Corynebacterium, Enterococcus, Lactococcus, Listeria,Micrococcus, Mycobacterium, Staphylococcus, or Streptococcus. In somecases, a biofouling-resistant coating disclosed herein prevents and/orreduces microfouling formed by a gram-positive bacterium: Actinomycesspp., Arthrobacter spp., Bacillus lichenformis, Clostridium difficile,Clostridium spp., Corynebacterium spp., Enterococcus faecalis,Lactococcus spp., Listeria monocytogenes, Micrococcus spp.,Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis,Streptococcus pneumoniae, or Streptococcus pyogenes.

In some cases, microfouling comprises bacteria adhesion. In someinstances, a biofouling-resistant coating disclosed herein preventsand/or reduces bacteria adhesion. In some cases, a biofouling-resistantcoating disclosed herein prevents and/or reduces bacteria adhesionformed by a gram-positive bacterium from the genus Actinomyces,Arthrobacter, Bacillus, Clostridium, Corynebacterium, Enterococcus,Lactococcus, Listeria, Micrococcus, Mycobacterium, Staphylococcus, orStreptococcus. In some cases, a biofouling-resistant coating disclosedherein coated onto a material prevents and/or reduces bacteria adhesionformed by a gram-positive bacterium: Actinomyces spp., Arthrobacterspp., Bacillus licheniformis, Clostridium difficile, Clostridium spp.,Corynebacterium spp., Enterococcus faecalis, Lactococcus spp., Listeriamonocytogenes, Micrococcus spp., Mycobacterium spp., Staphylococcusaureus, Staphylococcus epidermidis, Streptococcus pneumoniae, orStreptococcus pyogenes.

In some cases, microfouling comprises biofilm. In some instances, abiofouling-resistant coating disclosed herein coated onto a materialprevents and/or reduces biofilm. In some cases, a biofouling-resistantcoating disclosed herein coated onto a material prevents and/or reducesbiofilm formed by a gram-positive bacterium from the genus Actinomyces,Arthrobacter, Bacillus, Clostridium, Corynebacterium, Enterococcus,Lactococcus, Listeria, Micrococcus, Mycobacterium, Staphylococcus, orStreptococcus. In some cases, a biofouling-resistant coating disclosedherein coated onto a material prevents and/or reduces biofilm formed bya gram-positive bacterium: Actinomyces spp., Arthrobacter spp., Bacilluslicheniformis, Clostridium difficile, Clostridium spp., Corynebacteriumspp., Enterococcus faecalis, Lactococcus spp., Listeria monocytogenes,Micrococcus spp., Mycobacterium spp., Staphylococcus aureus,Staphylococcus epidermidis, Streptococcus pneumoniae, or Streptococcuspyogenes.

In some cases, microfouling is formed by a gram-negative bacterium.Exemplary gram-negative bacteria include, but are not limited to,bacteria from the genus Alteromonas, Aeromonas, Desulfovibrio,Escherichia, Fusobacterium, Geobacter, Haemophilus, Klebsiella,Legionella, Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella,Salmonella, or Vibrio. In some instances, a gram-negative bacteriumcomprises Alteromonas spp., Aeromonas spp., Desulfovibrio spp.,Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilusspp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp.,Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteuspenneri, Serratia spp., Shigella dysenteriae, Shigella flexneri,Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonellaenterica, or Vibrio Cholerae.

In some instances, microfouling is formed by a gram-negative bacteriumfrom the genus Alteromonas, Aeromonas, Desulfovibrio, Escherichia,Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella,Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, orVibrio. In some instances, microfouling is formed by a gram-negativebacterium: Alteromonas spp., Aeromonas spp., Desulfovibrio spp.,Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilusspp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp.,Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteuspenneri, Serratia spp., Shigella dysenteriae, Shigella flexneri,Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonellaenterica, or Vibrio Cholerae.

In some embodiments, a biofouling-resistant coating disclosed hereinprevents and/or reduces microfouling formed by a gram-negative bacteriumfrom the genus Alteromonas, Aeromonas, Desulfovibrio, Escherichia,Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella,Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, orVibrio. In some instances, a biofouling-resistant coating disclosedherein prevents and/or reduces microfouling formed by a gram-negativebacterium: Alteromonas spp., Aeromonas spp., Desulfovibrio spp.,Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilusspp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp.,Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteuspenneri, Serratia spp., Shigella dysenteriae, Shigella flexneri,Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonellaenterica, or Vibrio Cholerae.

In some embodiments, microfouling comprises bacteria adhesion. In someembodiments, a biofouling-resistant coating disclosed herein preventsand/or reduces bacteria adhesion formed by a gram-negative bacteriumfrom the genus Alteromonas, Aeromonas, Desulfovibrio, Escherichia,Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella,Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, orVibrio. In some instances, a biofouling-resistant coating disclosedherein prevents and/or reduces bacteria adhesion formed by agram-negative bacterium: Alteromonas spp., Aeromonas spp., Desulfovibriospp., Escherichia coli, Fusobacterium nucleatum, Geobacter spp.,Haemophilus spp., Klebsiella spp., Legionella pneumophila, Porphyromonasspp., Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis,Proteus penneri, Serratia spp., Shigella dysenteriae, Shigella flexneri,Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonellaenterica, or Vibrio Cholerae.

In some instances, microfouling comprises biofilm. In some embodiments,a biofouling-resistant coating disclosed herein prevents and/or reducesbiofilm formed by a gram-negative bacterium from the genus Alteromonas,Aeromonas, Desulfovibrio, Escherichia, Fusobacterium, Geobacter,Haemophilus, Klebsiella, Legionella, Porphyromonas, Proteus,Pseudomonas, Serratia, Shigella, Salmonella, or Vibrio. In someinstances, a biofouling-resistant coating disclosed herein preventsand/or reduces biofilm formed by a gram-negative bacterium: Alteromonasspp., Aeromonas spp., Desulfovibrio spp., Escherichia coli,Fusobacterium nucleatum, Geobacter spp., Haemophilus spp., Klebsiellaspp., Legionella pneumophila, Porphyromonas spp., Pseudomonasaeruginosa, Proteus vulgaris, Proteus mirabilis, Proteus penneri,Serratia spp., Shigella dysenteriae, Shigella flexneri, Shigella boydii,Shigella sonnei, Salmonella bongori, Salmonella enterica, or VibrioCholerae.

In some cases, microfouling is formed by a marine bacterium. In someinstances, a marine bacterium comprises Pseudoalteromonas spp. orShewanella spp. In some cases, microfouling is formed byPseudoalteromonas spp. or Shewanella spp.

In some embodiments, a biofouling-resistant coating disclosed hereinprevents and/or reduces microfouling formed by a marine bacterium. Insome cases, a biofouling-resistant coating disclosed herein preventsand/or reduces microfouling formed by Pseudoalteromonas spp. orShewanella spp.

In some instances, microfouling comprises bacteria adhesion. In someembodiments, a biofouling-resistant coating disclosed herein preventsand/or reduces bacteria adhesion formed by a marine bacterium. In somecases, a biofouling-resistant coating disclosed herein prevents and/orreduces bacteria adhesion formed by Pseudoalteromonas spp. or Shewanellaspp.

In some instances, microfouling comprises biofilm. In some embodiments,a biofouling-resistant coating disclosed herein prevents and/or reducesbiofilm formed by a marine bacterium. In some cases, abiofouling-resistant coating disclosed herein prevents and/or reducesbiofilm formed by Pseudoalteromonas spp. or Shewanella spp.

In some embodiments, microfouling is formed by a fungus. Exemplaryfungus includes, but is not limited to, Candida albicans, Candidaglabrata, Candida rugose, Candida parapsilosis, Candida tropicalis,Candida dubliniensis, or Hormoconis resinae. In some cases, microfoulingis formed by Candida albicans, Candida glabrata, Candida rugose, Candidaparapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconisresinae.

In some embodiments, a biofouling-resistant coating disclosed hereinprevents and/or reduces microfouling formed by a fungus. In some cases,a biofouling-resistant coating disclosed herein prevents and/or reducesmicrofouling formed by Candida albicans, Candida glabrata, Candidarugose, Candida parapsilosis, Candida tropicalis, Candida dubliniensis,or Hormoconis resinae.

In some instances, microfouling comprises bacteria adhesion. In someembodiments, a biofouling-resistant coating disclosed herein preventsand/or reduces bacteria adhesion formed by a fungus. In some cases, abiofouling-resistant coating disclosed herein prevents and/or reducesbacteria adhesion formed by Candida albicans, Candida glabrata, Candidarugose, Candida parapsilosis, Candida tropicalis, Candida dubliniensis,or Hormoconis resinae.

In some instances, microfouling comprises biofilm. In some embodiments,a biofouling-resistant coating disclosed herein prevents and/or reducesbiofilm formed by a fungus. In some cases, a biofouling-resistantcoating disclosed herein prevents and/or reduces biofilm formed byCandida albicans, Candida glabrata, Candida rugose, Candidaparapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconisresinae.

Macrofouling

In some embodiments, macrofouling comprises calcareous fouling organismor non-calcareous fouling organism. A calcareous fouling organism is anorganism with a hard body. In some cases, calcareous fouling organismscomprise barnacle, bryozoan, mollusk, polychaete, tube worm, or zebramussel. A non-calcareous fouling organism comprises a soft body.Non-calcareous fouling organism comprises seaweed, hydroids, or algae.

In some instances, macrofouling is formed by a calcareous foulingorganism. In some cases, macrofouling is formed by barnacle, bryozoan,mollusk, polychaete, tube worm, or zebra mussel.

In some embodiments, a biofouling-resistant coating disclosed hereinprevents and/or reduces macrofouling formed by a calcareous foulingorganism. In some instances, a biofouling-resistant coating disclosedherein prevents and/or reduces macrofouling formed by barnacle,bryozoan, mollusk, polychaete, tube worm, or zebra mussel.

In some cases, macrofouling is formed by a non-calcareous foulingorganism. In some cases, macrofouling is formed by seaweed, hydroids, oralgae.

In some embodiments, also disclosed herein are biofouling-resistantcoating preventing and/or reducing macrofouling formed by anon-calcareous fouling organism. In some instances, abiofouling-resistant coating disclosed herein prevents and/or reducesmacrofouling formed by seaweed, hydroids, or algae.

In some embodiments, a biofouling-resistant coating disclosed hereinreduces the formation of biofouling on its surface. In some cases, theformation of biofouling on a surface of a device modified with acompound of Formula (I), (II), or (III) is reduced by about 10%, 20%,30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%, 99.9%, or morerelative to the unmodified surface of a device. In some cases, theformation of biofouling on a surface of a device modified with acopolymer comprising a repeating unit of Formula (VII), (VIII), and (IX)is reduced by about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%,99%, 99.5%, 99.9%, or more relative to the unmodified surface of adevice. In some instances, the formation of biofouling is reduced by atleast about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%,99.5%, 99.9%, or more relative to the unmodified surface of a device. Insome instances, the formation of biofouling relative to the unmodifiedsurface of a device is determined by comparing the amount of biofoulingfollowing a period of time of storage, use, and/or testing of thedevice(s). For example, the devices may be tested by exposing them toconditions conducive of biofouling formation (e.g., in vitro biofoulingtesting techniques known and practiced in the art). In some instances,the formation of biofouling is reduced by about 10%, or more relative tothe unmodified surface of a device. In some instances, the formation ofbiofouling is reduced by about 20%, or more relative to the unmodifiedsurface of a device. In some instances, the formation of biofouling isreduced by about 30%, or more relative to the unmodified surface of adevice. In some instances, the formation of biofouling is reduced byabout 40%, or more relative to the unmodified surface of a device. Insome instances, the formation of biofouling is reduced by about 50%, ormore relative to the unmodified surface of a device. In some instances,the formation of biofouling is reduced by about 60%, or more relative tothe unmodified surface of a device. In some instances, the formation ofbiofouling is reduced by about 70%, or more relative to the unmodifiedsurface of a device. In some instances, the formation of biofouling isreduced by about 80%, or more relative to the unmodified surface of adevice. In some instances, the formation of biofouling is reduced byabout 90%, or more relative to the unmodified surface of a device. Insome instances, the formation of biofouling is reduced by about 95%, ormore relative to the unmodified surface of a device. In some instances,the formation of biofouling is reduced by about 99%, or more relative tothe unmodified surface of a device. In some instances, the formation ofbiofouling is reduced by about 99.5%, or more relative to the unmodifiedsurface of a device. In some instances, the formation of biofouling isreduced by about 99.9%, or more relative to the unmodified surface of adevice.

In some embodiments, a biofouling-resistant coating disclosed herein isfurther coated with an additional agent. In some instances, theadditional agent is an antimicrobial agent. Exemplary antimicrobialagent comprises quaternary ammonium salts or tertiary amines. In someinstances, the additional agent is a chemical disinfectant. Exemplarychemical disinfectant comprises sodium hypochlorite, sodium hydroxide,and benzalkonium chloride.

Definitions

As used herein, nomenclature for compounds, including organic compounds,can be given using common names, IUPAC, IUBMB, or CAS recommendationsfor nomenclature. When one or more stereochemical features are present,Cahn-Ingold-Prelog rules for stereochemistry can be employed todesignate stereochemical priority, E/Z specification, and the like. Oneof skill in the art can readily ascertain the structure of a compound ifgiven a name, either by systemic reduction of the compound structureusing naming conventions, or by commercially available software, such asCHEMDRAW™ (Cambridgesoft Corporation, U.S.A.).

As used in the specification and the appended claims, the singular forms“a,” “an” and “the” include plural referents unless the context clearlydictates otherwise. Thus, for example, reference to “a component,” “apolymer,” or “a particle” includes mixtures of two or more suchcomponents, polymers, or particles, and the like.

Ranges can be expressed herein as from “about” one particular value,and/or to “about” another particular value. When such a range isexpressed, another aspect includes from the one particular value and/orto the other particular value. Similarly, when values are expressed asapproximations, by use of the antecedent “about,” it will be understoodthat the particular value forms another aspect. It will be furtherunderstood that the endpoints of each of the ranges are significant bothin relation to the other endpoint, and independently of the otherendpoint. It is also understood that there are a number of valuesdisclosed herein, and that each value is also herein disclosed as“about” that particular value in addition to the value itself. Forexample, if the value “10” is disclosed, then “about 10” is alsodisclosed. In some embodiments, the term “about” includes an amount thatwould be expected to be within experimental error. It is also understoodthat when a value is disclosed that “less than or equal to” the value,“greater than or equal to the value” and possible ranges between valuesare also disclosed, as appropriately understood by the skilled artisan.For example, if the value “10” is disclosed the “less than or equal to10” as well as “greater than or equal to 10” is also disclosed. It isalso understood that throughout the application, data is provided in anumber of different formats and that this data represents endpoints andstarting points, and ranges for any combination of the data points. Forexample, if a particular data point “10” and a particular data point 15are disclosed, it is understood that greater than, greater than or equalto, less than, less than or equal to, and equal to 10 and 15 areconsidered disclosed as well as between 10 and 15. It is also understoodthat each unit between two particular units are also disclosed. Forexample, if 10 and 15 are disclosed, then 11, 12, 13, and 14 are alsodisclosed.

References in the specification and concluding claims to parts by weightof a particular element or component in a composition denotes the weightrelationship between the element or component and any other elements orcomponents in the composition or article for which a part by weight isexpressed. Thus, in a compound containing 2 parts by weight of componentX and 5 parts by weight component Y, X and Y are present at a weightratio of 2:5, and are present in such ratio regardless of whetheradditional components are contained in the compound.

A weight percent (wt. %) of a component, unless specifically stated tothe contrary, is based on the total weight of the formulation orcomposition in which the component is included.

As used herein, the terms “optional” or “optionally” means that thesubsequently described event or circumstance may or may not occur, andthat the description includes instances where said event or circumstanceoccurs and instances where it does not.

As used herein, the terms “effective amount” and “amount effective”refer to an amount that is sufficient to achieve the desired result orto have an effect on an undesired condition.

The term “stable”, as used herein, refers to compositions that are notsubstantially altered when subjected to conditions to allow for theirproduction, detection, and, in certain aspects, their recovery,purification, and use for one or more of the purposes disclosed herein.

As used herein, the term “polymer” refers to a relatively high molecularweight organic compound, natural or synthetic, whose structure can berepresented by a repeated small unit, the monomer (e.g., polyethylene,rubber, cellulose). Synthetic polymers are typically formed by additionor condensation polymerization of monomers. Unless indicated otherwise,polymer molecular weights are given in Daltons.

As used herein, the term “homopolymer” refers to a polymer formed from asingle type of repeating unit (monomer residue).

As used herein, the term “copolymer” refers to a polymer formed from twoor more different repeating units (monomer residues). By way of exampleand without limitation, a copolymer can be an alternating copolymer, arandom copolymer, a block copolymer, or a graft copolymer. It is alsocontemplated that, in certain aspects, various block segments of a blockcopolymer can themselves comprise copolymers. In some embodiments, theterms “copolymer” and “compound” are used interchangeably throughout thespecification.

As used herein, the term “oligomer” refers to a relatively low molecularweight polymer in which the number of repeating units is between two andten, for example, from two to eight, from two to six, or form two tofour. In one aspect, a collection of oligomers can have an averagenumber of repeating units of from about two to about ten, for example,from about two to about eight, from about two to about six, or formabout two to about four.

As used herein, the term “cross-linked polymer” refers to a polymerhaving bonds linking one polymer chain to another.

As used herein, the term “porogen composition” or “porogen(s)” refers toany structured material that can be used to create a porous material.

“Oxo” refers to the ═O substituent.

“Benzyl” refers to the —CH₂(C₆H₅) substituent.

“Alkyl” refers to a straight or branched hydrocarbon chain radical,having from one to twenty carbon atoms, and which is attached to therest of the molecule by a single bond. An alkyl comprising up to 10carbon atoms is referred to as a C₁-C₁₀ alkyl, likewise, for example, analkyl comprising up to 6 carbon atoms is a C₁-C₆ alkyl. Alkyls (andother moieties defined herein) comprising other numbers of carbon atomsare represented similarly. Alkyl groups include, but are not limited to,C₁-C₁₀ alkyl, C₁-C₉ alkyl, C₁-C₈ alkyl, C₁-C₇ alkyl, C₁-C₆ alkyl, C₁—Calkyl, C₁-C₄ alkyl, C₁-C₃ alkyl, C₁-C₂ alkyl, C₂-C₈ alkyl, C₃-C₈ alkyland C₄-C₈ alkyl. Representative alkyl groups include, but are notlimited to, methyl, ethyl, n-propyl, 1-methylethyl (i-propyl), n-butyl,i-butyl, s-butyl, n-pentyl, 1,1-dimethylethyl (t-butyl), 3-methylhexyl,2-methylhexyl, 1-ethyl-propyl, and the like. In some embodiments, thealkyl is methyl or ethyl. In some embodiments, the alkyl is —CH(CH₃)₂ or—C(CH₃)₃. Unless stated otherwise specifically in the specification, analkyl group may be optionally substituted as described below.

“Alkylene” or “alkylene chain” refers to a straight or branched divalenthydrocarbon chain linking the rest of the molecule to a radical group.In some embodiments, the alkylene is —CH₂—, —CH₂CH₂—, or —CH₂CH₂CH₂—. Insome embodiments, the alkylene is —CH₂—. In some embodiments, thealkylene is —CH₂CH₂—. In some embodiments, the alkylene is —CH₂CH₂CH₂—.In some embodiments, the alkylene is —CH₂C(CH₃)CH₂—.

“Alkoxy” refers to a radical of the formula —OR where R is an alkylradical as defined. Unless stated otherwise specifically in thespecification, an alkoxy group may be optionally substituted asdescribed below. Representative alkoxy groups include, but are notlimited to, methoxy, ethoxy, propoxy, butoxy, pentoxy. In someembodiments, the alkoxy is methoxy. In some embodiments, the alkoxy isethoxy.

“Alkenyl” refers to a type of alkyl group in which at least onecarbon-carbon double bond is present. In one embodiment, an alkenylgroup has the formula —C(R^(a))═C(R^(a))₂, wherein each R^(a) refers tothe remaining portions of the alkenyl group, which may be the same ordifferent. In some embodiments, each R^(a) is hydrogen or an alkylgroup. In some embodiments, an alkenyl is selected from ethenyl (i.e.,vinyl), propenyl (i.e., allyl), butenyl, pentenyl, pentadienyl, and thelike. Non-limiting examples of an alkenyl group include —CH═CH₂,—C(CH₃)═CH₂, —CH═CHCH₃, —C(CH₃)═CHCH₃, and —CH₂CH═CH₂.

“Heteroalkylene” refers to an alkyl radical as described above where oneor more carbon atoms of the alkyl is replaced with a O, N or S atom.“Heteroalkylene” or “heteroalkylene chain” refers to a straight orbranched divalent heteroalkyl chain linking the rest of the molecule toa radical group. Unless stated otherwise specifically in thespecification, the heteroalkyl or heteroalkylene group may be optionallysubstituted as described below. Representative heteroalkyl groupsinclude, but are not limited to —OCH₂OMe, —OCH₂CH₂OMe, or—OCH₂CH₂OCH₂CH₂NH₂. Representative heteroalkylene groups include, butare not limited to —OCH₂CH₂O—, —OCH₂CH₂OCH₂CH₂O—, or—OCH₂CH₂OCH₂CH₂OCH₂CH₂O—.

“Alkylamino” refers to a radical of the formula —NHR or —NRR where eachR is, independently, an alkyl radical as defined above. Unless statedotherwise specifically in the specification, an alkylamino group may beoptionally substituted as described below.

The term “aromatic” refers to a planar ring having a delocalized7-electron system containing 4n+2 π electrons, where n is an integer.Aromatics can be optionally substituted. The term “aromatic” includesboth aryl groups (e.g., phenyl, naphthalenyl) and heteroaryl groups(e.g., pyridinyl, quinolinyl).

“Aryl” refers to an aromatic ring wherein each of the atoms forming thering is a carbon atom. Aryl groups can be optionally substituted.Examples of aryl groups include, but are not limited to phenyl, andnaphthyl. In some embodiments, the aryl is phenyl. Depending on thestructure, an aryl group can be a monoradical or a diradical (i.e., anarylene group). Unless stated otherwise specifically in thespecification, the term “aryl” or the prefix “ar-” (such as in“aralkyl”) is meant to include aryl radicals that are optionallysubstituted.

“Carboxy” refers to —CO₂H. In some embodiments, carboxy moieties may bereplaced with a “carboxylic acid bioisostere”, which refers to afunctional group or moiety that exhibits similar physical and/orchemical properties as a carboxylic acid moiety. A carboxylic acidbioisostere has similar biological properties to that of a carboxylicacid group. A compound with a carboxylic acid moiety can have thecarboxylic acid moiety exchanged with a carboxylic acid bioisostere andhave similar physical and/or biological properties when compared to thecarboxylic acid-containing compound. For example, in one embodiment, acarboxylic acid bioisostere would ionize at physiological pH to roughlythe same extent as a carboxylic acid group. Examples of bioisosteres ofa carboxylic acid include, but are not limited to:

and the like.

“Cycloalkyl” refers to a monocyclic or polycyclic non-aromatic radical,wherein each of the atoms forming the ring (i.e. skeletal atoms) is acarbon atom. Cycloalkyls may be saturated, or partially unsaturated.Cycloalkyls may be fused with an aromatic ring (in which case thecycloalkyl is bonded through a non-aromatic ring carbon atom).Cycloalkyl groups include groups having from 3 to 10 ring atoms.Representative cycloalkyls include, but are not limited to, cycloalkylshaving from three to ten carbon atoms, from three to eight carbon atoms,from three to six carbon atoms, or from three to five carbon atoms.Monocyclic cycloalkyl radicals include, for example, cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Insome embodiments, the monocyclic cycloalkyl is cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl. In some embodiments, the monocycliccycloalkyl is cyclopentyl. Polycyclic radicals include, for example,adamantyl, norbornyl, decalinyl, and 3,4-dihydronaphthalen-1(2H)-one.Unless otherwise stated specifically in the specification, a cycloalkylgroup may be optionally substituted.

“Fluoroalkyl” refers to an alkyl in which one or more hydrogen atoms arereplaced by a fluorine atom. In one aspect, a fluoroalkyl is a C₁-C₆fluoroalkyl. In some embodiments, a fluoroalkyl is selected fromtrifluoromethyl, difluoromethyl, fluoromethyl, 2,2,2-trifluoroethyl,1-fluoromethyl-2-fluoroethyl, and the like.

“Fused” refers to any ring structure described herein which is fused toan existing ring structure. When the fused ring is a heterocyclyl ringor a heteroaryl ring, any carbon atom on the existing ring structurewhich becomes part of the fused heterocyclyl ring or the fusedheteroaryl ring may be replaced with a nitrogen atom.

“Halo” or “halogen” refers to bromo, chloro, fluoro or iodo.

“Haloalkyl” refers to an alkyl radical, as defined above, that issubstituted by one or more halo radicals, as defined above, e.g.,trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl,2,2,2-trifluoroethyl, 1,2-difluoroethyl, 3-bromo-2-fluoropropyl,1,2-dibromoethyl, and the like. Unless stated otherwise specifically inthe specification, a haloalkyl group may be optionally substituted.

“Haloalkoxy” refers to an alkoxy radical, as defined above, that issubstituted by one or more halo radicals, as defined above, e.g.,trifluoromethoxy, difluoromethoxy, fluoromethoxy, trichloromethoxy,2,2,2-trifluoroethoxy, 1,2-difluoroethoxy, 3-bromo-2-fluoropropoxy,1,2-dibromoethoxy, and the like. Unless stated otherwise specifically inthe specification, a haloalkoxy group may be optionally substituted.

“Heterocycloalkyl” or “heterocyclyl” or “heterocyclic ring” refers to astable 3- to 14-membered non-aromatic ring radical comprising 2 to 10carbon atoms and from one to 4 heteroatoms selected from the groupconsisting of nitrogen, oxygen, and sulfur. Unless stated otherwisespecifically in the specification, the heterocycloalkyl radical may be amonocyclic, or bicyclic ring system, which may include fused (when fusedwith an aryl or a heteroaryl ring, the heterocycloalkyl is bondedthrough a non-aromatic ring atom) or bridged ring systems. The nitrogen,carbon or sulfur atoms in the heterocyclyl radical may be optionallyoxidized. The nitrogen atom may be optionally quaternized. Theheterocycloalkyl radical is partially or fully saturated. Examples ofsuch heterocycloalkyl radicals include, but are not limited to,dioxolanyl, thienyl[1,3]dithianyl, decahydroisoquinolyl, imidazolinyl,imidazolidinyl, isothiazolidinyl, isoxazolidinyl, morpholinyl,octahydroindolyl, octahydroisoindolyl, 2-oxopiperazinyl,2-oxopiperidinyl, 2-oxopyrrolidinyl, oxazolidinyl, piperidinyl,piperazinyl, 4-piperidonyl, pyrrolidinyl, pyrazolidinyl, quinuclidinyl,thiazolidinyl, tetrahydrofuryl, trithianyl, tetrahydropyranyl,thiomorpholinyl, thiamorpholinyl, 1-oxo-thiomorpholinyl,1,1-dioxo-thiomorpholinyl. The term heterocycloalkyl also includes allring forms of carbohydrates, including but not limited tomonosaccharides, disaccharides and oligosaccharides. Unless otherwisenoted, heterocycloalkyls have from 2 to 10 carbons in the ring. In someembodiments, heterocycloalkyls have from 2 to 8 carbons in the ring. Insome embodiments, heterocycloalkyls have from 2 to 8 carbons in the ringand 1 or 2 N atoms. In some embodiments, heterocycloalkyls have from 2to 10 carbons, 0-2 N atoms, 0-2 O atoms, and 0-1 S atoms in the ring. Insome embodiments, heterocycloalkyls have from 2 to 10 carbons, 1-2 Natoms, 0-1 O atoms, and 0-1 S atoms in the ring. It is understood thatwhen referring to the number of carbon atoms in a heterocycloalkyl, thenumber of carbon atoms in the heterocycloalkyl is not the same as thetotal number of atoms (including the heteroatoms) that make up theheterocycloalkyl (i.e. skeletal atoms of the heterocycloalkyl ring).Unless stated otherwise specifically in the specification, aheterocycloalkyl group may be optionally substituted.

“Heteroaryl” refers to an aryl group that includes one or more ringheteroatoms selected from nitrogen, oxygen and sulfur. The heteroaryl ismonocyclic or bicyclic. Illustrative examples of monocyclic heteroarylsinclude pyridinyl, imidazolyl, pyrimidinyl, pyrazolyl, triazolyl,pyrazinyl, tetrazolyl, furyl, thienyl, isoxazolyl, thiazolyl, oxazolyl,isothiazolyl, pyrrolyl, pyridazinyl, triazinyl, oxadiazolyl,thiadiazolyl, furazanyl, indolizine, indole, benzofuran, benzothiophene,indazole, benzimidazole, purine, quinolizine, quinoline, isoquinoline,cinnoline, phthalazine, quinazoline, quinoxaline, 1,8-naphthyridine, andpteridine. Illustrative examples of monocyclic heteroaryls includepyridinyl, imidazolyl, pyrimidinyl, pyrazolyl, triazolyl, pyrazinyl,tetrazolyl, furyl, thienyl, isoxazolyl, thiazolyl, oxazolyl,isothiazolyl, pyrrolyl, pyridazinyl, triazinyl, oxadiazolyl,thiadiazolyl, and furazanyl. Illustrative examples of bicyclicheteroaryls include indolizine, indole, benzofuran, benzothiophene,indazole, benzimidazole, purine, quinolizine, quinoline, isoquinoline,cinnoline, phthalazine, quinazoline, quinoxaline, 1,8-naphthyridine, andpteridine. In some embodiments, heteroaryl is pyridinyl, pyrazinyl,pyrimidinyl, thiazolyl, thienyl, thiadiazolyl or furyl.

In some embodiments, a heteroaryl contains 0-4 N atoms in the ring. Insome embodiments, a heteroaryl contains 1-4 N atoms in the ring. In someembodiments, a heteroaryl contains 0-4 N atoms, 0-1 O atoms, and 0-1 Satoms in the ring. In some embodiments, a heteroaryl contains 1-4 Natoms, 0-1 O atoms, and 0-1 S atoms in the ring. In some embodiments,heteroaryl is a C1-C9heteroaryl. In some embodiments, monocyclicheteroaryl is a C1-C5heteroaryl. In some embodiments, monocyclicheteroaryl is a 5-membered or 6-membered heteroaryl. In someembodiments, a bicyclic heteroaryl is a C6-C9heteroaryl.

The term “optionally substituted” or “substituted” means that thereferenced group may be substituted with one or more additional group(s)individually and independently selected from alkyl, haloalkyl,cycloalkyl, aryl, heteroaryl, heterocycloalkyl, —OH, alkoxy, aryloxy,alkylthio, arylthio, alkylsulfoxide, arylsulfoxide, alkylsulfone,arylsulfone, —CN, alkyne, C₁-C₆alkylalkyne, halogen, acyl, acyloxy,—CO₂H, —CO₂alkyl, nitro, and amino, including mono- and di-substitutedamino groups (e.g. —NH₂, —NHR, —N(R)₂), and the protected derivativesthereof. In some embodiments, optional substituents are independentlyselected from alkyl, alkoxy, haloalkyl, cycloalkyl, halogen, —CN, —NH₂,—NH(CH₃), —N(CH₃)₂, —OH, —CO₂H, and —CO₂alkyl. In some embodiments,optional substituents are independently selected from fluoro, chloro,bromo, iodo, —CH₃, —CH₂CH₃, —CF₃, —OCH₃, and —OCF₃. In some embodiments,substituted groups are substituted with one or two of the precedinggroups. In some embodiments, an optional substituent on an aliphaticcarbon atom (acyclic or cyclic, saturated or unsaturated carbon atoms,excluding aromatic carbon atoms) includes oxo (═O). Compounds describedherein can contain one or more double bonds and, thus, potentially giverise to cis/trans (E/Z) isomers, as well as other conformationalisomers. Unless stated to the contrary, the compounds disclosed hereininclude all such possible isomers, as well as mixtures of such isomers.

In some embodiments, PSB and PFPA-PSB are used interchangeably and referto poly(sulfobetaine methacrylate-co-perfluorophenylazide methacrylate).

Certain materials, compounds, compositions, and components disclosedherein can be obtained commercially or readily synthesized usingtechniques generally known to those of skill in the art. For example,the starting materials and reagents used in preparing the disclosedcompounds and compositions are either available from commercialsuppliers such as Aldrich Chemical Co., Milwaukee, Wis.), Acros Organics(Morris Plains, N.J.), Fisher Scientific (Pittsburgh, Pa.), or Sigma(St. Louis, Mo.) or are prepared by methods known to those skilled inthe art following procedures set forth in references such as Fieser andFieser's Reagents for Organic Synthesis, Volumes 1-17 (John Wiley andSons, 1991); Rodd's Chemistry of Carbon Compounds, Volumes 1-5 andSupplemental volumes (Elsevier Science Publishers, 1989); OrganicReactions, Volumes 1-40 (John Wiley and Sons, 1991); March's AdvancedOrganic Chemistry, (John Wiley and Sons, 4th Edition); and Larock'sComprehensive Organic Transformations (VCH Publishers Inc., 1989).

Unless otherwise expressly stated, it is in no way intended that anymethod set forth herein be construed as requiring that its steps beperformed in a specific order. Accordingly, where a method claim doesnot actually recite an order to be followed by its steps or it is nototherwise specifically stated in the claims or descriptions that thesteps are to be limited to a specific order, it is no way intended thatan order be inferred, in any respect. This holds for any possiblenon-express basis for interpretation, including: matters of logic withrespect to arrangement of steps or operational flow; plain meaningderived from grammatical organization or punctuation; and the number ortype of embodiments described in the specification.

Examples

The following examples are provided for illustrative purposes only, andare intended to be purely exemplary of the disclosure and are notintended to limit the scope of the claims provided herein. Efforts havebeen made to ensure accuracy with respect to numbers (e.g., amounts,temperature, etc.), but some errors and deviations should be accountedfor.

Materials

α-Bromoisobutyryl bromide, N-Boc-ethanolamine, Trifluoroacetic acid,1,1,4,7,10,10-Hexamethyltriethylenetetramine (97%), [2-(Methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide, tetrabutylammoniumchloride, and cupper(I) chloride are used as received from SigmaAldrich. Sodium bicarbonate, methylene chloride, magnesium sulfate, and2,2,2-trifluoroethanol are purchased from Alfa Aesar. Sylgard 184 kit(Dow Corning) is obtained from Fisher Chemical.

The zwitterionic polymer, polysulfobetaine (PSB), is selected as anantifouling component of the coating. By adsorbing waterelectrostatically, PSB coatings form a thin hydration barrier thatprevents organic material from adhering to its surface. Commonly usedapproaches to attach PSB coatings to surfaces such as radical-initiatedgraft polymerizations of PSB-methacrylate necessitate the use ofoxygen-free conditions, preconditioning steps, or long reaction timesthat do not meet the scalability requirements. To circumvent the use ofair-free graft polymerizations, we employ perfluorophenylazide (PFPA) asa molecular anchor to graft the PSB coating to the surface of polymericmaterials under ambient conditions. When triggered with UV-light, PFPAmoieties generate a highly reactive nitrene that forms covalent bondswith materials containing amines, C═C double bonds, and C—H bonds. Withthis method, it is surprisingly found that PSB is rapidly coated to avariety of substrates using UV light under ambient conditions with nopreconditioning steps needed. In addition, it is unexpectedly found thatwater provides an optimal solvent for photografting of PFPA-PSB coatingand that photografting of PFPA-PSB does not proceed well in the presenceof organic solvents.

Example 1. Synthesis of ATRP Initiator 2-Aminoethyl 2-Bromoisobutyrate

ATRP initiator 2-aminoethyl 2-bromoisobutyrate is synthesized accordingto the following procedure. 5 g of 2-bromoisobutyryl bromide is added toa solution of 3.8 g of t-Boc-aminoethyl alcohol and 2.5 g oftriethylamine in 12 ml methylene chloride in an ice bath. After 16 h,the salts are filtered off and the filtrate is extracted with saturatedsodium bicarbonate solution. Methylene chloride phase is dried overmagnesium sulfate and evaporated. The resulting t-Boc-aminoethyl2-bromoisobutyrate is treated by 15 ml trifluoroacetic acid (TFA) for 2h and crystallized upon addition of ethyl ether.

Example 2. Synthesis of PFPAS-Methacrylate/acrylate

2-Aminoethyl methacrylate/acrylate hydrochloride is dissolved in DIWater at a concentration of 0.56M. 2 equivalents of sodium bicarbonateis added dropwise to the solution. In a separate vial, 1 equivalent ofpentafluorobenzene sulfonyl chloride is dissolved in acetone at aconcentration of 0.186M. Both solutions are cooled to 4° C. The solutioncontaining 2-aminoethyl methacrylate/acrylate and sodium bicarbonate isadded to the pentafluorobenzenesulfonyl chloride solution dropwise onice. The reaction is stirred and gradually warmed up to roomtemperature. After 3 hours, 3 equivalents of sodium azide is added tothe solution and the reaction is stirred for another 18 hours at roomtemperature. After, the acetone is removed under reduced pressure. Threetimes the reaction volume of methyl tert-butyl ether is added to thecrude mixture and poured into a separatory funnel. DI water is addedthree times to wash the organic layer. The methyl tert-butyl ether isremoved under reduced pressure to give the desired product.

Example 3. Synthesis ofPFPAA-Methacrylate/methacrylamide/acrylate/acrylamide

4-azidotetrafluorobenzoic acid was prepared according a publishedprocedure by Keana et al. (J. Org. Chem. 1990, 55(11), 3640-7). Toprepare the PFPAA-methacrylate: N-3-aminopropylmethacrylatehydrochloride and triethylamine are dissolved in dichloromethane to aconcentration of 0.31M each. This solution is allowed to stir for 3hours. The 4-azidotetrafluorobenzoic acid is then dissolved at aconcentration of 0.235M. 4-dimethylaminopyridine is then added to thesolution containing the 4-azidotetrafluorobenzoic acid (0.26M). A secondportion of triethylamine is added so that the final concentration oftriethylamine in the reaction is 0.56M. The reaction is then stirred for48 hours, washed 3× with DI water, and the organic layer evaporatedunder reduced pressure to give the desired product. This procedure isused to prepare different PFPAamide—methacrylate/methacrylamide/acrylate/acrylamide compounds.

Example 4. Synthesis ofPFPAE-methaerylate/niethacrylamide/acrylate/acrylaniide

4-azidotetrafluorobenzoic acid was prepared according a publishedprocedure by Keana et al. (J. Org. Chem. 1990, 55(11), 3640-7). Toprepare the PFPAE-methacrylamide: 2-Hydroxyethyl methacrylamide andtriethylamine are dissolved in dichloromethane to a concentration of0.31M each. This solution is allowed to stir for 3 hours. The4-azidotetrafluorobenzoic acid is then dissolved at a concentration of0.235M. 4-dimethylaminopyridine is then added to the solution containingthe 4-azidotetrafluorobenzoic acid (0.26M). A second portion oftriethylamine is added so that the final concentration of triethylaminein the reaction is 0.56M. The reaction is then stirred for 48 hours,washed 3× with DI water, and the organic layer evaporated under reducedpressure to give the desired product. This procedure is used to preparedifferent PFPA ester—methacrylate/methacrylamide/acrylate/acrylamidecompounds.

Example 5. Copolymer formation by polymerization of sulfobetainemethacrylate and perfluorophenylazide

The copolymer is synthesized as follows: 2 g sulfobetaine methacrylatemonomer 5-1, 100 mg, 150 mg, or 200 mg of perfluorophenylazide monomer5-2, and 2 g tetrabutylammonium chloride are dissolved in 30 mLtrifluoroethanol in a Schlenk flask and undergo two vacuum-argon cycles.Then, 14 mg Cu(I)Cl and 76 μL1,1,4,7,10,10-hexamethyltriethylenetetramine are added. The Schlenkflask is sealed with a rubber septum and another two vacuum-argon cyclesare performed. Finally, 44 mg TFA protected 2-aminoethyl2-bromoisobutyrate as ATRP initiator is dissolved in a small amount oftrifluoroethanol (˜0.5 mL) and syringe-injected into the Schlenk flask,followed by two additional vacuum-argon cycles. Polymerization iscarried out at 60° C. under argon. After 24 h, the reaction mixture iscooled down to room temperature and the copolymer is purified byperforming membrane dialysis using a membrane with cut off molecularweight of 1000 Dalton. The resulting copolymer is freeze-dried beforefurther use.

NMR spectra are recorded on a Bruker DPX300 spectrometer. Chemicalshifts are calibrated to residual solvent signals. Molecular weights anddispersities are measured by gel permeation chromatography on a ShimadzuHPLC system with a refractive index detector S3 RID-10A, one TosohTSKGel guard column, and one Tosoh TSKGel G4000PW column. Eluent is 0.1M NaNO₃+20 mM phosphate buffer pH 7+20% MeCN at 25° C. (flow rate 0.7mL/min). Calibration is performed using near-monodisperse PEG standardsfrom Polymer Laboratories. Light scattering is used to obtain theabsolute molecular weight.

Example 6. Synthesis of mixed charged copolymers

Monomers 6-2, 6-3, and 6-4 are dissolved in different molar ratios in asolution of 4:1 TFE:DMF at a total concentration of 0.37M. 6-1 is addedat a concentration of 0.022M and the radical initiator (AIBN) is addedat a concentration of 0.0037M. The reaction is performed protected underargon gas using common Schlenk line technique. The oxygen is removedunder reduced pressure and back-filled with argon gas three times. Thereaction is stirred by mechanical stir bar and is heated to 60° C. usingoil bath. After 72 h, the reaction solvent is removed under reducedpressure with a rotary evaporator to ¼th of the original reactionvolume. Once concentrated, the polymer crude mixture is diluted with 10times its volume with DI water. Residual monomers and oligomers areremoved by pipetting the crude polymer reaction mixture into cellulosedialysis bags, with a 10,000 Dalton molecular weight cut-off, andplacing the filled dialysis bag into a large water bath. The water bathis replenished with fresh deionized water continuously over 7 days. Thepurified polymer solution, now dispersed in water inside the dialysisbags, are freeze-dried to remove the water to yield a white powder. Tosynthesize mixed charged copolymers of different isoelectric points, themolar ratios of 6-2, 6-3, and 6-4 can be modified.

Example 7. Synthesis of mixed charged copolymers

Monomers 6-3 and 6-4 are dissolved in different molar ratios in asolution of 4:1 TFE:DMF at a total concentration of 0.37M. 6-1 is addedat a concentration of 0.022M and the radical initiator (AIBN) is addedat a concentration of 0.0037M. The reaction is performed protected underargon gas using common Schlenk line technique. The oxygen is removedunder reduced pressure and back-filled with argon gas three times. Thereaction is stirred by mechanical stir bar and is heated to 60° C. usingoil bath. After 72 h, the reaction solvent is removed under reducedpressure with a rotary evaporator to ¼th of the original reactionvolume. Once concentrated, the polymer crude mixture is diluted with 10times its volume with DI water. Residual monomers and oligomers areremoved by pipetting the crude polymer reaction mixture into cellulosedialysis bags, with a 10,000 Dalton molecular weight cut-off, andplacing the filled dialysis bag into a large water bath. The water bathis replenished with fresh deionized water continuously over 7 days. Thepurified polymer solution, now dispersed in water inside the dialysisbags, are freeze-dried to remove the water to yield a white powder. Tosynthesize mixed charged copolymers of different isoelectric points, themolar ratios of 6-3 and 6-4 can be modified.

Example 8. Synthesis of PFPA-Positive and PFPA-Negative ChargedCopolymers

A surface containing a 1:1 molar ratio of positive and negative moietiesis hypothesized to possess great antifouling properties. To achieve the1:1 molar ratio of positive and negative moieties on the surface, twoseparate copolymers can be polymerized, each copolymer containing eitherpositive charged moieties or negative charged moieties, and thenblending them together in a 1:1 molar ratio in solution. An example ofthis is demonstrated below.

To synthesize a negatively charged PFPA-sulfonic acid copolymer, monomer6-3 is dissolved in a solution of 4:1 TFE:DMF at a concentration of0.37M. 6-1 is added at a concentration of 0.022M and the radicalinitiator (AIBN) is added at a concentration of 0.0037M. The reaction isperformed protected under argon gas using common Schlenk line technique.The oxygen is removed under reduced pressure and back-filled with argongas three times. The reaction is stirred by mechanical stir bar and isheated to 60° C. using oil bath. After 72 h, the reaction solvent isremoved under reduced pressure with a rotary evaporator to ¼th of theoriginal reaction volume. Once concentrated, the polymer crude mixtureis diluted with 10 times its volume with Deionized water. Residualmonomers and oligomers are removed by pipetting the crude polymerreaction mixture into cellulose dialysis bags, with a 10,000 Daltonmolecular weight cut-off, and placing the filled dialysis bag into alarge water bath. The water bath is replenished with fresh deionizedwater continuously over 7 days. The purified polymer solution, nowdispersed in water inside the dialysis bags, are freeze-dried to removethe water to yield a white powder.

To synthesize a positively charged PFPA-quaternary ammonium copolymer,monomer 6-4 is dissolved in a solution of 4:1 TFE:DMF at a concentrationof 0.37M. 6-1 is added at a concentration of 0.022M and the radicalinitiator (AIBN) is added at a concentration of 0.0037M. The reaction isperformed protected under argon gas using common Schlenk line technique.The oxygen is removed under reduced pressure and back-filled with argongas three times. The reaction is stirred by mechanical stir bar and isheated to 60° C. using oil bath. After 72 h, the reaction solvent isremoved under reduced pressure with a rotary evaporator to ¼th of theoriginal reaction volume. Once concentrated, the polymer crude mixtureis diluted with 10 times its volume with Deionized water. Residualmonomers and oligomers are removed by pipetting the crude polymerreaction mixture into cellulose dialysis bags, with a 10,000 Daltonmolecular weight cut-off, and placing the filled dialysis bag into alarge water bath. The water bath is replenished with fresh deionizedwater continuously over 7 days. The purified polymer solution, nowdispersed in water inside the dialysis bags, are freeze-dried to removethe water to yield a white powder.

Once powders of each of the positively charged copolymer and negativelycharged copolymer are obtained, they can be each added into a suitablesolvent (H₂O, DMF, 2,2,2-trifluoroethanole, DMSO, DMAc, etc) to make a1:1 molar ratio of sulfonic acid moieties and quaternary ammoniummoieties. The resulting mixture is used to modify a surface.

Example 9. UV Light Silicone Surface Modification and Characterization

Copolymer of Example 5 or 6 is dissolved or suspended in DI water toprepare 2-20 mg/mL aqueous mixture. Silicone elastomer films areprepared by mixing 10:1 (by weight) base: crosslinker (Sylgard 184),followed by degassing under vacuum and subsequently crosslinking at 70°C. for 8 h. For anti-biofouling experiments, 2 mg/mL of copolymeraqueous mixture is spread onto a cured silicone elastomer surface andexposed to 254 nm UV light irradiation for 10 mins. Then the siliconeelastomer surface is rinsed with large amounts of DI water to removeunreacted and physically adsorbed copolymer molecules from the surfaceand stored underneath a layer of water before further use.

Contact angles of deionized water (18 MΩ/cm, Millipore) on polymercoatings are measured using a rame-hart Model 590 goniometer. Advancingangles (θ_(adv)) are measured as water is supplied via a syringe, whilereceding angles (θ_(rec)) are measured as water is removed via asyringe. The total drop volume is about 5 μL, and the pump dispensingspeed is about 0.2 μL/s. Measurements are taken over three or moredifferent locations on each surface, and the reported values are in theformat of average standard deviation.

For surface modification, the following photoreaction takes place.First, PFPA decomposes by releasing N₂ to give the singlet phenylnitreneupon activation of the compound by UV light. The singlet phenylnitrenefurther undergoes C—H or N—H insertion, and C═C addition reactions whichcontributes to the covalent bond formation with the target surfaces(Liu, L.-H. et al. Perfluorophenyl azides: new applications in surfacefunctionalization and nanomaterial synthesis. Accounts of ChemicalResearch 2010, 43 (11), 1434-1443). In this process, “the singletphenylnitrene” reaction intermediate is a strong nucleophile and itsstability is not affected by the existence of oxygen and watermolecules.

Example 10. Silicone Surface Heat Modification and Characterization

Four 2 cm segments of a catheter (16fr) were immersed in a 10 mg/mLsolution of PFPA-PSB copolymer dissolved in DI water in a sealed flaskand subjected to a 1 h heating period at various temperatures (80° C.,100° C., 120° C., 140° C., 160° C., 180° C., 200° C., or 220° C.). Thecatheter segments were then removed from the solution and rinsed byslowly dipping twice in fresh DI water and blotted on a paper towel toremove any liquid from the interior lumens of the samples. The catheterswere then allowed to dry

A dye solution of 3 mg/mL Crystal Violet-HCl solution in DI water wasstirred overnight. The modified catheter segments and an analogous setof unmodified catheter segments were immersed individually in thecrystal violet solution for 1 minute and then rinsed by dipping twice infresh DI water blotted on a paper towel to remove any liquid from theinterior lumens of the samples. The catheter segments were then placedinto scintillation vials.

10 mL of a 2:1 solution of DI Water: Acetic Acid was then added to eachvial. Each vial was shaken vigorously for 30 seconds to remove alladsorbed crystal violet from the catheters. 2 mL of solution was removedfrom each tube, placed into a cuvette, and the absorbance at 580 nm wastaken. Because the initial readings were too high, each solution wasthen diluted by a factor of 2. The absorbance measurement at 580 nm forthe unmodified (control) and modified catheters by thermal treatment atdifferent temperatures are listed in Table E-10 below.

TABLE E-10 T, ° C. Absorbances at 580 nm N/A 0.104 (control)  80 0.296100 0.347 120 0.492 140 0.458 160 0.615 180 0.685 200 0.652 220 1.486

Example 11. Substrates Modification and Characterization

Coating substrates with PSB: PDMS substrates are prepared by mixing a10:1 ratio of elastomer to curing agent, followed by curing at 80° C.for 1 h. The PDMS disks are cut with a laser cutter into 3 mm diameterdisks. 30 μL of coating (PSB) mixture with concentrations 2, 5, or 10 mgmL⁻¹ is placed and spread out on the surface of each disk. The PSB isthen crosslinked on the discs by exposing them to 254 nm UV light for 10min under sterile conditions, followed by rinsing with Milli-Q water anddrying with air.

Contact angle visualization and measurement: Water contact angle onvarious substrates, such as PDMS, Nylon 66, polystyrene, polyvinylchloride, and polyethylene is visualized by placing 17 μL of Milli-Qwater on the flat substrates at room temperature followed by imagingthem. The images are analyzed using Fta32 version 2.1 software tomeasure the contact angle. To study the recovery of water contact angleon PDMS substrates, they are divided into two groups: (i) uncoated PDMSsheets, which are treated using 02 plasma (Plasma Etch PE25-JW PlasmaCleaner, Nev., US) for 1 min, followed by measuring water contact angleafter 1, 2, 4, 7, and 10 days, and (ii) PDMS sheets that are coated withPSB, and the contact angle is similarly measured over time.

XPS studies are carried out on a Kratos AXIS Ultra DLD with amonochromatic Al Kα X-ray source operating at 10 mA and 15 kV. Surveyspectra and individual high-resolution spectra are collected using passenergies of 160 and 20 eV, respectively. Data processing are performedusing CasaXPS 2.3 software, and spectra binding energies are calibratedby assigning the hydrocarbon peak in the C1s high-resolution spectra to284.6 eV

Cell culture: NIH/3T3 fibroblast cells are cultured in cell cultureflasks containing DMEM with 10% FBS and 1% P/S and passaged twice aweek. For this purpose, a standard cell culture incubator (Thermo FisherScientific, PA, USA) is used to provide 5% CO₂ atmosphere andtemperature=37° C. To conduct cell studies, 0.5% trypsin-EDTA is used totrypsinize fibroblast cells and count them using a hemocytometer,followed by seeding them on desirable substrates.

Cell adhesion: Trypsinized fibroblasts cells are seeded on PSB-coated96-well plates by placing 100 μL of the cell suspension (cell density˜1×10⁵ in 1 mL media) on the treated well plates, cultured for 24 h.Uncoated well plates are used as a control.

Cytotoxicity evaluation: To assess the cytotoxicity of un-crosslinkedPSB, trypsinized fibroblasts cells are seeded on 96-well plates byplacing 100 μL of the cell suspension (cell density ˜1×10⁵ in 1 mLmedia) and cultured for 24 h, followed by adding a desired amount ofun-crosslinked PSB to the media and further culturing for 72 h. Thecytotoxicity of crosslinked PSB is evaluated by seeding 500 μL of cellsuspension (cell density ˜2×10⁵ in 1 mL media) in 24-well plates,culturing for 24 h, followed by placing PSB coated PDMS discs (diameter˜6 mm, height 3 mm) in the medium and further culturing for 72 h.

Metabolic activity assessment: MTT((3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide) (ThermoFisher Scientific) stain solutions are prepared at a concentration ˜5 mgmL⁻¹ in DPBS. Cell culture media are removed from the well plates,followed by one time rinsing with DPBS. The wells are then loaded withfresh media and MTT solution at a ratio of 9:1. The well plates arewrapped with aluminum foil and incubated for 4 h at 37° C. and 5% CO₂.After 4 h, the wells are aspirated with a pipette and 200 or 500 μL ofDMSO is added for 96- and 24-well plates, respectively. The well platesare wrapped with aluminum foil again and left on a rotator for 30 min,after which absorbance is recorded at 570 nm using a microplate reader(Synergy HTX multi-mode reader, BioTek, VT, USA).

Live/Dead assay: To assess the cell viability, a live/dead fluorescenceassay is used. The staining solution is prepared by adding ethidiumhomodimer-1 (20 μL) and calcein AM (5 μL) to DPBS (10 mL). To performthe assay, the cells are incubated with 1 mL of the staining solutionfor approximately 20 min and imaged using a fluorescent microscope (AxioObserver 5, Zeiss, Germany) at excitation/emission wavelengths 494/515nm for calcein and 528/617 nm for ethidium homodimer-1.

Protein adsorption: The protein adsorption is assessed by incubating 100μg of 50 μg mL of Alexa Fluor™ 488 (AF)-conjugated BSA on each PDMSsubstrate for 1 h at 37° C. To inhibit the photodegradation of AF,aluminum foil is used to wrap the substrates. Then, the PDMS substratesare gently rinsed with Milli-Q water and imaged at a constant exposuretime 1.13 ms using a fluorescent microscope (Axio Observer 5, Zeiss,Germany) at excitation/emission wavelengths 488/517 nm. ImageJ (NationalInstitutes of Health, US) is used to quantify the emitted fluorescencevia the mean gray value analysis tool. The average pixel brightnessindirectly reflects the amount of protein adsorbed to the substrates.Background autofluorescence is eliminated using AF-free samples ascontrol.

Bacterial culture: Bacterial species, E. coli, S. epidermidis, S. aureusRosenbach, S. aureus (MRSA), P. aeruginosa, and C. albicans are used inthis work. All strains are incubated at 30° C. at 150 rpm until amid-exponential phase is reached, at which time the cells are harvestedby centrifugation at 3800×g for 8 min. E. coli is grown on aLuria-Bertani (LB) broth, S. epidermidis, P. aeruginosa, and S. aureusRosenbach are grown on nutrient broth; S. aureus (MRSA) is grown on atrypticase soy broth (TSB); and C. albicans is grown on a yeast mold(YM) broth. These initial cultures are then adjusted to an opticaldensity of 1 at 600 nm and had an initial total cell number ranging from1×10⁷ cells per mL to 1×10⁸ cells per mL.

Bacterial adhesion: 55 mm diameter Petri dishes are filled with a 10:1elastomer to curing agent (Sylgard 184) and allowed to cure at roomtemperature for at least 48 hours to form a 3 mm thick PDMS film on thebottom of the dishes. Modified plates are coated with a solutioncontaining PFPA-PSB and irradiated with 254 nm UV light. Each modifiedand unmodified PDMS-lined dish is inoculated with 4 mL of bacterial orfungal suspension and incubated for 24-72 hours (shaken at 25 rpm) at35° C. The bacterial or fungal suspension is then removed and stored forfurther microscopy. The Petri dishes are gently rinsed with sterile,deionized water using a Pasteur pipette, and covered in 4 mL of a dyesolution (SYTO 9 live/dead Baclight Bacterial Viability Kit L13152,Molecular Probes) for 15 min. The SYTO 9 solution is prepared bydissolving the contents of component A of the kit in 30 mL of sterile,deionized water. After the staining is complete, the Petri dishes aregently rinsed with deionized water and imaged using a 4×CCD camera(Axiocam MRm System) attached to a Zeiss Axioskop 2 microscope with a10× objective, 40× objective, a fluorescent lamp, and a blue excitationfilter. During observation, the images are taken at an excitation rangeof 450-490 nm. The number of attached microorganisms on all fluorescentimages are determined using ImageJ software.

Statistical analysis: The data are reported as mean values standarddeviation of at least triplicate experiments. The one-way analysis ofvariance (ANOVA) and Tukey's multiple comparisons are used, andstatistically significant differences are identified for p-values lowerthan 0.05 (*p<0.05), 0.01 (**p<0.01), 0.001 (***p<0.001), and 0.0001(****p<0.0001).

Escherichia coli is used as the model bacteria for this test. Purebacterial cell cultures are suspended in Luria-Bertani (LB) broth andgrown at 35° C. while being shaken at 150 rpm and incubated until amid-exponential phase is reached, at which time the cells are harvestedby centrifugation at 3800×g for 8 min. The cells are then re-suspendedwith fresh LB medium to a concentration of 4×10⁷ cells/mL. Membranecoupons, of approximately 1 cm², are incubated in this bacterialsuspension for 24 hr at 25 rpm and 35° C. The coupons are then removedfrom the suspension and gently rinsed with fresh LB broth using aPasteur pipette. Once rinsed, the coupons are immersed in a dye solution(SYTO 9 live/dead Baclight Bacterial Viability Kit L13152, MolecularProbes) for 15 min. The SYTO 9 solution is prepared by dissolving thecontents of component A of the kit in 30 mL of sterile distillatedwater. After the staining is complete, the coupons are gently rinsedwith fresh LB broth and imaged using a microscope (Olympus BX51microscope) equipped with a fluorescent lamp and green/red fluorescencefilters and a 4×CCD camera attachment (FVIEW-II, Soft Imaging System,USA).

While preferred embodiments of the present disclosure have been shownand described herein, it will be obvious to those skilled in the artthat such embodiments are provided by way of example only. Numerousvariations, changes, and substitutions will now occur to those skilledin the art without departing from the disclosure. It should beunderstood that various alternatives to the embodiments of thedisclosure described herein may be employed in practicing thedisclosure. It is intended that the following claims define the scope ofthe disclosure and that methods and structures within the scope of theseclaims and their equivalents be covered thereby.

Numbered Embodiments

Embodiment 1 is a compound that has the structure of Formula (I):

wherein

-   A is selected from —C(═O)—, —S(═O)—, —S(═O)₂—, and —S(═O)(—NR³)—;-   L is selected from —OQ, —NR³Q, and —N(R³)₂Q⁺;-   Q is a structure represented by a formula:

-   -   Z is selected from —CR^(6a)R^(6b)—, —C(═O)—, —C(═NH)—, and        —C(═NH)NR⁷—;    -   m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each R³ is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄ alkyl,        optionally substituted aryl, and —X-optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(4a), R^(4b), R^(5a), R^(5c), R^(6a), and R^(6b) is        independently selected from hydrogen, halogen, —CN, —OH,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted aryl, —NR^(8a)R^(8b),        —NR^(8a)R^(8b)R^(8c+), —S(═O)₂O⁻, —S(═O)₂OR⁹, —C(═O)O⁻, and        —C(═O)OR⁹;    -   R^(5b) is —OR^(10b), —NR^(10a)R^(10b), or        —NR^(10a)R^(10b)R^(10c+);    -   each R⁷, R^(8a), R^(8b), R^(8c), and R⁹ is independently        selected from hydrogen and optionally substituted C1-C₄ alkyl,        and optionally substituted aryl;    -   each R^(10a) and R^(10c) is independently selected from        hydrogen, optionally substituted C₁-C₄ alkyl, optionally        substituted aryl, -(optionally substituted        C₁-C₈alkylene)S(═O)₂O⁻, -(optionally substituted        C₁-C₈alkylene)S(═O)₂OH, -(optionally substituted        C₁-C₈alkylene)C(═O)O⁻, and -(optionally substituted        C₁-C₈alkylene)C(═O)OH; and    -   R^(10b) is —C(═O)—C₂-C₆alkenyl, —S(═O)—C₂-C₆alkenyl, or        —S(═O)₂—C₂-C₆alkenyl; provided that a compound of Formula (I) is        not        N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide;    -   N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide; or    -   2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

Embodiment 2 is the compound of embodiment 1, wherein the compound has astructure selected from:

Embodiment 3 is the compound of embodiment 1 or 2, wherein the compoundhas a structure selected from:

Embodiment 4 is the compound of any one of embodiments 1-3, wherein thecompound has a structure selected from:

Embodiment 5 is the compound of embodiment 1, wherein the compound hasthe structure selected from:

Embodiment 6 is the compound of embodiment 1, wherein the compound hasthe following structure:

Embodiment 7 is the compound of embodiment 5 or 6, wherein R^(1a),R^(1b), R^(2a), and R^(2b) are each —F.

Embodiment 8 is the compound of any one of embodiments 1-7, wherein Z is—CR^(6a)R^(6b)—.

Embodiment 9 is the compound of embodiment 8, wherein R^(6a) and R^(6b)are each hydrogen.

Embodiment 10 is the compound of any one of embodiments 1-9, wherein mis 0, 1, 2, or 3.

Embodiment 11 is the compound of embodiment 10, wherein m is 0.

Embodiment 12 is the compound of any one of embodiments 1-11, whereinR^(5a) is hydrogen; R^(5b) is —NR^(10a)R^(10b); and R^(5c) is hydrogen.

Embodiment 13 is the compound of any one of embodiments 1-11, whereinR^(5a) is hydrogen; R^(5b) is —OR^(10b); and R^(5c) is hydrogen.

Embodiment 14 is the compound of embodiment 1, wherein the compound hasthe structure of Formula (Ia):

Embodiment 15 is the compound of embodiment 1, wherein the compound hasthe structure of Formula (Ib):

Embodiment 16 is the compound of embodiment 1, wherein the compound ofFormula (I) has a structure of Formula (Ic):

Embodiment 17 is the compound of embodiment 1, wherein the compound ofFormula (I) has a structure of Formula (Id):

Embodiment 18 is the compound of any one of embodiments 1-17, whereinR^(10a) is hydrogen.

Embodiment 19 is the compound of embodiment 1, wherein the compound ofFormula (I) has a structure of Formula (Ie):

Embodiment 20 is the compound of embodiment 1, wherein the compound ofFormula (I) has a structure of Formula (If):

Embodiment 21 is the compound of embodiment 1, wherein the compound ofFormula (I) has a structure of Formula (Ig):

Embodiment 22 is the compound of embodiment 1, wherein the compound ofFormula (I) has a structure of Formula (Ih):

Embodiment 23 is the compound of any one of embodiments 1-15, 19, or 20,wherein R³ is hydrogen.

Embodiment 24 is a compound that has the structure of Formula (II):

wherein

-   -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C1-C6fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3c) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OH,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   x is 0.001-0.999; and    -   wherein the compounds of Formula (II) is charged or        zwitterionic;        provided that a compound of Formula (II) is not

Embodiment 25 is the compound of embodiment 24, wherein each R^(1a) andR^(1b) is independently halogen.

Embodiment 26 is the compound of embodiment 24 or 25, wherein eachR^(1a) and R^(1b) is independently F or Cl.

Embodiment 27 is the compound of any one of embodiments 24-26, whereinR^(1a) and R^(1b) are each F.

Embodiment 28 is the compound of any one of embodiments 24-27, whereineach R^(2a) and R^(2b) is independently selected from halogen, —CN, and—CF₃;

Embodiment 29 is the compound of any one of embodiments 24-28, whereineach R^(2a) and R^(2b) is independently selected from F, Cl, —CN, and—CF₃;

Embodiment 30 is the compound of any one of embodiments 24-29, whereinR^(2a) and R^(2b) are each F.

Embodiment 31 is the compound of any one of embodiments 24-30, wherein Ais —S(═O)₂—; A² is —C(═O)—; and A³ is —C(═O)—.

Embodiment 32 is the compound of any one of embodiments 24-31, whereinB¹ and B² are each —NR^(3c)—.

Embodiment 33 is the compound of embodiment 32, wherein R^(3c) ishydrogen or —CH₃.

Embodiment 34 is the compound of embodiment 33, wherein R^(3c) ishydrogen.

Embodiment 35 is the compound of any one of embodiments 24-34, whereinB³ is —O—.

Embodiment 36 is the compound of any one of embodiments 24-35, wherein Dis —S(═O)₂OR^(9a) or —C(═O)OR^(9a).

Embodiment 37 is the compound of embodiment 36 wherein R^(9a) ishydrogen or —CH₃.

Embodiment 38 is the compound of any one of embodiments 24-35, wherein Dis —S(═O)₂O— or —C(═O)O—.

Embodiment 39 is the compound of embodiment 38, wherein D is —S(═O)₂O⁻.

Embodiment 40 is the compound of any one of embodiments 24-39, whereineach R^(6c) and R^(6d) is hydrogen.

Embodiment 41 is the compound of any one of embodiments 24-40, whereineach R^(3a) and R^(3b) is —CH₃.

Embodiment 42 is the compound of any one of embodiments 24-41, whereinR^(11a) is hydrogen or —CH₃.

Embodiment 43 is the compound of embodiment 42, wherein R^(11a) is —CH₃.

Embodiment 44 is the compound of any one of embodiments 24-43, whereinR^(12a) is hydrogen or —CH₃.

Embodiment 45 is the compound of embodiment 44, wherein R^(12a) is —CH₃.

Embodiment 46 is the compound of any one of embodiments 24-45, whereineach R^(11b), R^(11c), R^(12b), and R^(12c) is hydrogen.

Embodiment 47 is a compound that has the structure of Formula (III):

wherein

-   -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+)        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a);    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   x is 0.001-0.999.

Embodiment 48 is the compound of embodiment 47, wherein each R^(1a) andR^(1b) is independently halogen.

Embodiment 49 is the compound of embodiment 47 or 48, wherein eachR^(1a) and R^(1b) is independently F or Cl.

Embodiment 50 is the compound of any one of embodiments 47-49, whereinR^(1a) and R^(1b) are each F.

Embodiment 51 is the compound of any one of embodiments 47-50, whereineach R^(2a) and R^(2b) is independently selected from halogen, —CN, and—CF₃;

Embodiment 52 is the compound of any one of embodiments 47-51, whereineach R^(2a) and R^(2b) is independently selected from F, Cl, —CN, and—CF₃;

Embodiment 53 is the compound of any one of embodiments 47-52, whereinR^(2a) and R^(2b) are each F.

Embodiment 54 is the compound of any one of embodiments 47-53, wherein Ais —S(═O)₂—; A² is —C(═O)—; and A³ is —C(═O)—.

Embodiment 55 is the compound of any one of embodiments 47-54, whereinB¹ and B² are each —NR^(3c)—.

Embodiment 56 is the compound of embodiment 55, wherein R^(3c) ishydrogen or —CH₃.

Embodiment 57 is the compound of embodiment 56, wherein R^(3c) ishydrogen.

Embodiment 58 is the compound of any one of embodiments 47-57, whereinB³ is —NR^(3c)—.

Embodiment 59 is the compound of embodiment 58, wherein R^(3c) ishydrogen.

Embodiment 60 is the compound of any one of embodiments 47-59, wherein Eis —NR^(9a)R^(9b)R^(9c+) or —S(═O)₂OR^(9a).

Embodiment 61 is the compound of embodiment 60, wherein E is—NR^(9a)R^(9b)R^(9c+).

Embodiment 62 is the compound of embodiment 61, wherein each R^(9a),R^(9b), and R^(9c) is hydrogen or —CH₃.

Embodiment 63 is the compound of embodiment 62, wherein each R^(9a),R^(9b), and R^(9c) is hydrogen.

Embodiment 64 is the compound of embodiment 62, wherein each R^(9a),R^(9b), and R^(9c) is —CH₃.

Embodiment 65 is the compound of embodiment 60, wherein E is—S(═O)₂OR^(9a).

Embodiment 66 is the compound of embodiment 65, wherein R^(9a) ishydrogen or —CH₃.

Embodiment 67 is the compound of embodiment 66, wherein each R^(9a) ishydrogen.

Embodiment 68 is the compound of embodiment 66, wherein each R^(9a) is—CH₃.

Embodiment 69 is the compound of any one of embodiments 47-68, whereineach R^(6c) and R^(6d) is independently selected from hydrogen and —CH₃.

Embodiment 70 is the compound of any one of embodiments 47-69, whereineach R^(3a) and R^(3b) is —CH₃.

Embodiment 71 is the compound of any one of embodiments 47-70, whereinR^(11a) is hydrogen or —CH₃.

Embodiment 72 is the compound of embodiment 71, wherein R^(11a) is —CH₃.

Embodiment 73 is the compound of any one of embodiments 47-72, whereinR^(12a) is hydrogen or —CH₃.

Embodiment 74 is the compound of embodiment 73, wherein R^(12a) is —CH₃.

Embodiment 75 is the compound of any one of embodiments 47-74, whereineach R^(11b), R^(11c), R^(12b), and R^(12c) is hydrogen.

Embodiment 76 is a copolymer comprising:

-   -   a) a repeating unit of Formula (VII):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹ and A² is independently selected from —C(═O)—, —S(═O)—,        —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹ and B² is independently selected from —O— and —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), and R^(11c) is independently        selected from hydrogen, optionally substituted C₁-C₄ alkyl, and        optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and    -   s is an integer selected from 1, 2, 3, 4, and 5;    -   b) a repeating unit of Formula (VIII):

-   -   wherein,    -   A³ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;    -   B³ is —O— or —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(6c) and R^(6d) is independently selected from hydrogen,        halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,        optionally substituted C₁-C₄ fluoroalkyl, optionally substituted        C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a),        —C(═O)O⁻, and —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(12a), R^(12b), and R^(12c) is independently        selected from hydrogen, optionally substituted    -   C₁-C₄ alkyl, and optionally substituted aryl;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5; and    -   wherein the repeating unit of Formula (VIII) is charged or        zwitterionic; and    -   c) a repeating unit of Formula (IX):

-   -   A⁴ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;    -   B⁴ is —O— or —NR^(3c)—;    -   Z⁴ is —(CR^(6c)R^(6d))_(k)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+)        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a);    -   each R^(6c), and R^(6d) is independently selected from hydrogen,        halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,        optionally substituted C₁-C₄ fluoroalkyl, optionally substituted        C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a),        —C(═O)O⁻, and —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(13a), R^(13b) and R^(13c) is        independently selected from hydrogen, optionally substituted        C₁-C₄ alkyl, and optionally substituted aryl; and    -   k is an integer selected from 1, 2, 3, 4, or 5.

Embodiment 77 is the copolymer of embodiment 76, wherein each R^(1a) andR^(1b) is independently halogen.

Embodiment 78 is the copolymer of embodiment 76 or 77, wherein eachR^(1a) and R^(1b) is independently F or Cl.

Embodiment 79 is the copolymer of any one of embodiments 76-78, whereineach R^(1a) and R^(1b) is F.

Embodiment 80 is the copolymer of any one of embodiments 76-79, whereineach R^(2a) and R^(2b) is independently selected from halogen, —CN, and—CF₃.

Embodiment 81 is the copolymer of any one of embodiments 76-80, whereineach R^(2a) and R^(2b) is independently selected from F, Cl, —CN, and—CF₃.

Embodiment 82 is the copolymer of any one of embodiments 76-81, whereineach R^(2a) and R^(2b) is F.

Embodiment 83 is the copolymer of any one of embodiments 76-82, whereinA is —S(═O)₂— and each A², A³, and A⁴ is —C(═O)—.

Embodiment 84 is the copolymer of any one of embodiments 76-83, whereineach B¹, B², and B³ is independently —O— or —NR^(3c)—.

Embodiment 85 is the copolymer of any one of embodiments 76-84, whereineach R^(3c) is hydrogen or —CH₃.

Embodiment 86 is the copolymer of any one of embodiments 76-85, whereinD is —S(═O)₂O⁻ or —C(═O)O⁻.

Embodiment 87 is the copolymer of any one of embodiments 76-86, whereinE is —NR^(9a)R^(9b)R^(9c+) or —S(═O)₂OR^(9a).

Embodiment 88 is the copolymer of any one of embodiments 76-87, whereineach R^(9a), R^(9b), and R^(9c) is independently hydrogen or C₁-C₄alkyl.

Embodiment 89 is the copolymer of any one of embodiments 76-88, whereineach R^(3a) and R^(3b) is —CH₃.

Embodiment 90 is the copolymer of any one of embodiments 76-89, whereineach R^(4c), R^(4d), R^(5d), and R^(5e) is hydrogen.

Embodiment 91 is the copolymer of any one of embodiments 76-90, whereineach R^(3c), R^(3d), R^(6c), and R^(6d) is hydrogen.

Embodiment 92 is the copolymer of any one of embodiments 76-91, whereineach R^(11a), R^(12a), and R^(13a) is hydrogen or —CH₃.

Embodiment 93 is the copolymer of any one of embodiments 76-92, whereineach R^(11b), R^(11c), R^(12b), R^(12c), R^(13b), and R^(13c) ishydrogen.

Embodiment 94 is the copolymer of any one of embodiments 76-93, whereinn is 0, 1, or 2.

Embodiment 95 is the copolymer of any one of embodiments 76-94, whereineach s, t, p, and k is independently 1, 2 or 3.

Embodiment 96 is a medical device coated with a compound of any one ofembodiments 1-95.

Embodiment 97 is a biofouling-resistant medical device, wherein asurface of the medical device is coated with a phenyl azide-basedcopolymer having a number-average molecular weight of between about10,000 and about 250,000.

Embodiment 98 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 10,000 and about 20,000.

Embodiment 99 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 10,000 and about 40,000.

Embodiment 100 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 20,000 and about 60,000.

Embodiment 101 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 40,000 and about 100,000.

Embodiment 102 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 80,000 and about 160,000.

Embodiment 103 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 120,000 and about 200,000.

Embodiment 104 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 14,000 and about 21,000.

Embodiment 105 is the biofouling-resistant medical device of embodiment97, wherein the phenyl azide-based copolymer has a number-averagemolecular weight of between about 15,000 and about 18,000.

Embodiment 106 is the biofouling-resistant medical device of any one ofembodiments 97-105, wherein the phenyl azide-based copolymer is acompound of any one of embodiments 24-75 or a copolymer of any one ofembodiments 76-95.

Embodiment 107 is a biofouling-resistant medical device, wherein asurface of the medical device is coated with a phenyl azide-basedcopolymer having a polydispersity index (PDI) of between about 1 and1.5.

Embodiment 108 is the biofouling-resistant medical device of embodiment107, wherein the PDI is about 1.4, 1.3, 1.2, or 1.1.

Embodiment 109 is the biofouling-resistant medical device of embodiment107, wherein the PDI is about 1.19.

Embodiment 110 is the biofouling-resistant medical device of any one ofembodiments 97-109, wherein the medical device comprises a dentalinstrument or a medical instrument.

Embodiment 111 is the biofouling-resistant medical device of any one ofembodiments 97-110, wherein the medical device comprises an implant, anIV, a prosthesis, suturing material, valve, stent, catheter, rod, shunt,scope, a contact lens, tubing, wiring, electrode, clip, fastener,syringe, container, or a combination thereof.

Embodiment 112 is the biofouling-resistant medical device of embodiment111, wherein the medical device is a contact lens.

Embodiment 113 is the biofouling-resistant medical device of embodiment111, wherein the medical device is catheter.

Embodiment 114 is the biofouling-resistant medical device of embodiment113, wherein the catheter is an indwelling catheter.

Embodiment 115 is the biofouling-resistant medical device of embodiment113, wherein the catheter comprises an uretic catheter or a Foleycatheter.

Embodiment 116 is the biofouling-resistant medical device of embodiment111, wherein the medical device is scope.

Embodiment 117 is the biofouling-resistant medical device of embodiment116, wherein the scope comprises a scope utilized in an image-guidedsurgery.

Embodiment 118 is the biofouling-resistant medical device of embodiment116, wherein the scope comprises a scope utilized in endoscopy orlaparoscopy.

Embodiment 119 is the biofouling-resistant medical device of embodiment110 or 111, wherein the medical device comprises auditory prostheses,artificial larynx, dental implants, mammary implants, penile implants,cranio/facial tendons, tendons, ligaments, menisci, or disks.

Embodiment 120 is the biofouling-resistant medical device of any one ofembodiments 110, 111, or 119, wherein the medical device comprisesartificial bones, artificial joints, or artificial organs.

Embodiment 121 is the biofouling-resistant medical device of embodiment120, wherein the artificial organs comprise artificial pancreas,artificial hearts, artificial limbs, or heart valves.

Embodiment 122 is the biofouling-resistant medical device of any one ofembodiments 97-109, wherein the medical device comprises a bandage or apatch.

Embodiment 123 is the biofouling-resistant medical device of any one ofembodiments 107-122, wherein the phenyl azide-based copolymer comprisesa compound of any one of embodiments 1-75 or a copolymer of any one ofembodiments 76-95.

Embodiment 124 is the biofouling-resistant medical device of any one ofembodiments 107-122, wherein the copolymer comprises zwitterioniccopolymer.

Embodiment 125 is the biofouling-resistant medical device of embodiment124, wherein the zwitterionic copolymer is polysulfobetaine.

Embodiment 126 is the biofouling-resistant medical device of any one ofembodiments 107-125, wherein the biofouling is produced by a bacterium,a virus, and/or a fungus.

Embodiment 127 is a method of making a biofouling-resistant medicaldevice, comprising:

-   -   a) contacting a surface of a medical device with a solution or        suspension comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the medical device of step a) with a        light source for a time sufficient to undergo photografting of        the charged or zwitterion copolymer onto the surface of the        medical device, thereby making the biofouling-resistant medical        device;        wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and    -   wherein the charged or zwitterion copolymer having a        number-average molecular weight of between about 10,000 and        about 250,000.

Embodiment 128 is a method of making a charged or zwitterion copolymermodified biofouling-resistant device comprising:

-   -   a) contacting a surface of a silicon-based device with a        solution or suspension comprising a charged or zwitterion        copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the        silicon-based device, thereby generating the charged or        zwitterion copolymer modified device;        wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer.

Embodiment 129 is a method of making a charged or zwitterion copolymermodified biofouling-resistant device comprising:

-   -   a) contacting a surface of a device with a solution or        suspension comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the device,        thereby generating the charged or zwitterion copolymer modified        device;        wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and    -   wherein the charged or zwitterion copolymer having a        number-average molecular weight of between about 10,000 and        about 250,000.

Embodiment 130 is the method of any one of embodiments 127-129, whereinthe time sufficient to undergo photografting is at least 1 minute, atleast 2 minutes, 3 minutes, 4 minutes, 5 minutes, 6 minutes, 7 minutes,8 minutes, 9 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes or30 minutes.

Embodiment 131 is the method of any one of embodiments 127-130, whereinthe light source is an ultraviolet light source.

Embodiment 132 is the method of embodiment 131, wherein the ultravioletlight source has an intensity of at least 900 μW/cm².

Embodiment 133 is the method of embodiment 131 or 132, wherein theultraviolet light source has a wavelength of between 240 nm and 280 nm,between 240 nm and 275 nm, between 240 nm and 270 nm, between 240 nm and265 nm, between 240 nm and 260 nm, between 240 nm and 255 nm, between240 nm and 250 nm, between 240 nm and 245 nm, between 250 nm and 280 nm,between 250 nm and 275 nm, between 250 nm and 270 nm, between 250 nm and265 nm, between 250 nm and 260 nm, between 255 nm and 280 nm, between255 nm and 275 nm, between 255 nm and 270 nm, between 255 nm and 265 nm,between 255 nm and 260 nm, between 260 nm and 280 nm, between 260 nm and275 nm, between 260 nm and 270 nm, or between 270 nm and 280 nm.

Embodiment 134 is the method of embodiment 131 or 132, wherein theultraviolet light source has a wavelength of at least 240 nm, 245 nm,250 nm, 251 nm, 252 nm, 253 nm, 254 nm, 255 nm, 256 nm, 257 nm, 258 nm,259 nm, 260 nm, 261 nm, 262 nm, 263 nm, 264 nm, 265 nm, 266 nm, 267 nm,268 nm, 269 nm, 270 nm, 275 nm or 280 nm.

Embodiment 135 is the method of any one of embodiments 127-134, whereinthe solution or suspension of step a) is an aqueous solution orsuspension.

Embodiment 136 is the method of any one of embodiments 127-135, whereinphotografting of step b) is not affected by the presence of oxygen.

Embodiment 137 is the method of any one of embodiments 127-136, whereinthe charged or zwitterion copolymer is a compound of any one ofembodiments 24-75 or a copolymer of any one of embodiments 76-95.

Embodiment 138 is the method of any one of the embodiments 127-137,wherein the solution or suspension comprising a charged or zwitterioncopolymer has a concentration of the charged or zwitterion copolymer inthe solution or suspension between 1 mg/mL and 30 mg/mL.

Embodiment 139 is the method of embodiment 138, wherein theconcentration of the charged or zwitterion copolymer in the solution orsuspension is between 1 mg/mL and 25 mg/mL, between 1 mg/mL and 20mg/mL, between 1 mg/mL and 15 mg/mL, between 1 mg/mL and 10 mg/mL,between 1 mg/mL and 5 mg/mL, between 5 mg/mL and 30 mg/mL, between 5mg/mL and 25 mg/mL, between 5 mg/mL and 20 mg/mL, between 5 mg/mL and 15mg/mL, between 5 mg/mL and 10 mg/mL, between 10 mg/mL and 30 mg/mL,between 10 mg/mL and 25 mg/mL, between 10 mg/mL and 20 mg/mL, between 10mg/mL and 15 mg/mL, between 15 mg/mL and 30 mg/mL, between 15 mg/mL and25 mg/mL, between 15 mg/mL and 20 mg/mL, between 20 mg/mL and 30 mg/mL,or between 20 mg/mL and 25 mg/mL.

Embodiment 140 is the method of embodiment 138, wherein theconcentration of the charged or zwitterion copolymer in the solution orsuspension is about 1 mg/mL, 2 mg/mL, 3 mg/mL, 4 mg/mL, 5 mg/mL, 6mg/mL, 7 mg/mL, 8 mg/mL, 9 mg/mL, 10 mg/mL, 11 mg/mL, 12 mg/mL, 13mg/mL, 14 mg/mL, 15 mg/mL, 16 mg/mL, 17 mg/mL, 18 mg/mL, 19 mg/mL, 20mg/mL, 21 mg/mL, 22 mg/mL, 23 mg/mL, 24 mg/mL, 25 mg/mL, 26 mg/mL, 27mg/mL, 28 mg/mL, 29 mg/mL, or 30 mg/mL.

Embodiment 141 is the method of any one of embodiments 127-140, whereinthe concentration of the charged or zwitterion copolymer is between 0.1to 1 mg per square centimeter of the device.

Embodiment 142 is the method of embodiment 128, wherein the charged orzwitterion copolymer has a number-average molecular weight of betweenabout 10,000 and about 250,000

Embodiment 143 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 10,000 and about 20,000.

Embodiment 144 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 10,000 and about 40,000.

Embodiment 145 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 20,000 and about 60,000.

Embodiment 146 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 40,000 and about 100,000.

Embodiment 147 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 80,000 and about 160,000.

Embodiment 148 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 120,000 and about 200,000.

Embodiment 149 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 14,000 and about 21,000.

Embodiment 150 is the method of any one of embodiments 127 or 129-142,wherein the charged or zwitterion copolymer has a number-averagemolecular weight of between about 15,000 and about 18,000.

Embodiment 151 is the method of embodiment 127 or 129, wherein thedevice comprises a carbon-based device or a silicon-based device.

Embodiment 152 is the method of embodiment 151, wherein the devicecomprises a silicon-based device.

Embodiment 153 is the method of embodiment 128 or 152, wherein thesilicon-based device comprises a silicon-based polymer moiety.

Embodiment 154 is the method of embodiment 153, wherein thesilicon-based polymer moiety comprises siloxane polymer moiety,sesquisiloxane polymer moiety, siloxane-silarylene polymer moiety,silalkylene polymer moiety, polysilane moiety, polysilylene moiety, orpolysilazane moiety.

Embodiment 155 is the method of embodiment 154, wherein thesilicon-based device comprises siloxane polymer moiety.

Embodiment 156 is the method of embodiment 151, wherein the devicecomprises a carbon-based device.

Embodiment 157 is the method of embodiment 156, wherein the carbon-baseddevice comprises a carbon-based polymer.

Embodiment 158 is the method of embodiment 156, wherein the carbon-baseddevice comprises a polyolefin moiety.

Embodiment 159 is the method of embodiment 158, wherein the polyolefinmoiety comprises polyethylene moiety, polypropylene moiety, polyvinylchloride moiety, polyvinylidene fluoride moiety, polytetrafluoroethylenemoiety, polychlorotrifluoroethylene moiety, or polystyrene moiety.

Embodiment 160 is the method of embodiment 157, wherein the carbon-basedpolymer comprises polyamide moiety, polyurethane moiety,phenol-formaldehyde resin moiety, polycarbonate moiety, polychloroprenemoiety, polyacrylonitrile moiety, polyimide moiety, or polyester moiety.

Embodiment 161 is the method of embodiment 157, wherein the carbon-basedpolymer comprises nylon.

Embodiment 162 is the method of embodiment 157, wherein the carbon-basedpolymer comprises polyethylene terephthalate.

Embodiment 163 is the method of any one of embodiments 127-162, whereinthe copolymer comprises zwitterionic copolymer.

Embodiment 164 is the method of embodiment 163, wherein the zwitterioniccopolymer is polysulfobetaine.

Embodiment 165 is the method of any one of embodiments 127-164, whereinthe biofouling is produced by a bacterium, a virus, and/or a fungus.

Embodiment 166 is a method for synthesizing a compound of Formula (II)comprising: reacting a compound of Formula (IV) or a salt or solvatethereof with a compound of Formula (V):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OH,        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), R^(11c), R^(12a), R^(12b), and        R^(12c) is independently selected from hydrogen, optionally        substituted C₁-C₄ alkyl, and optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5;    -   x is 0.001-0.999; and    -   wherein the compounds of Formula (II) and Formula (V) are each        independently charged or zwitterionic;    -   provided that a compound of Formula (II) is not

Embodiment 167 is the method of embodiment 166, wherein each R^(1a) andR^(1b) is independently halogen.

Embodiment 168 is the method of embodiment 166 or 167, wherein eachR^(1a) and R^(1b) is independently F or Cl.

Embodiment 169 is the method of any one of embodiments 166-168, whereinR^(1a) and R^(1b) are each F.

Embodiment 170 is the method of any one of embodiments 166-169, whereineach R^(2a) and R^(2b) is independently selected from halogen, —CN, and—CF₃;

Embodiment 171 is the method of any one of embodiments 166-170, whereineach R^(2a) and R^(2b) is independently selected from F, Cl, —CN, and—CF₃;

Embodiment 172 is the method of any one of embodiments 166-171, whereinR^(2a) and R^(2b) are each F.

Embodiment 173 is the method of any one of embodiments 166-172, whereinA is —S(═O)₂—; A² is —C(═O)—; and A³ is —C(═O)—.

Embodiment 174 is the method of any one of embodiments 166-173, whereinB¹ and B² are each —NR^(3c)—.

Embodiment 175 is the method of embodiment 174, wherein R^(3c) ishydrogen or —CH₃.

Embodiment 176 is the method of embodiment 175, wherein R^(3c) ishydrogen.

Embodiment 177 is the method of any one of embodiments 166-176, whereinB³ is —O—.

Embodiment 178 is the method of any one of embodiments 166-177, whereinD is —S(═O)₂OR^(9a) or —C(═O)OR^(9a).

Embodiment 179 is the method of embodiment 178, wherein R^(9a) ishydrogen or —CH₃.

Embodiment 180 is the method of any one of embodiments 166-177, whereinD is —S(═O)₂O⁻ or —C(═O)O⁻.

Embodiment 181 is the method of embodiment 180, wherein D is —S(═O)₂O⁻.

Embodiment 182 is the method of any one of embodiments 166-181, whereineach R^(6c) and R^(6d) is hydrogen.

Embodiment 183 is the method of any one of embodiments 166-182, whereineach R^(3a) and R^(3b) is —CH₃.

Embodiment 184 is the method of any one of embodiments 166-183, whereinR^(11a) is hydrogen or —CH₃.

Embodiment 185 is the method of embodiment 184, wherein R^(11a) is —CH₃.

Embodiment 186 is the method of any one of embodiments 166-185, whereinR^(12a) is hydrogen or —CH₃.

Embodiment 187 is the method of embodiment 186, wherein R^(12a) is —CH₃.

Embodiment 188 is the method of any one of embodiments 166-187, whereineach R^(11b), R^(11c), R^(12b), and R^(12C) is hydrogen.

Embodiment 189 is a method for synthesizing a compound of Formula (III)comprising: reacting a compound of Formula (IV) or a salt or solvatethereof with a compound of Formula (VI):

wherein

-   -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹, A², and A³ is independently selected from —C(═O)—,        —S(═O)—, —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹, B², and B³ is independently selected from —O— and        —NR^(3c)—;    -   Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+)        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a);    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(11a), R^(11b), R^(11c), R^(12a),        R^(12b), and R^(12c) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8    -   s is an integer selected from 1, 2, 3, 4, or 5;    -   t is an integer selected from 1, 2, 3, 4, or 5; and    -   x is 0.001-0.999.

Embodiment 190 is the method of embodiment 189, wherein each R^(1a) andR^(1b) is independently halogen.

Embodiment 191 is the method of embodiment 189 or 190, wherein eachR^(1a) and R^(1b) is independently F or Cl.

Embodiment 192 is the method of any one of embodiments 189-191, whereinR^(1a) and R^(1b) are each F.

Embodiment 193 is the method of any one of embodiments 189-192, whereineach R^(2a) and R^(2b) is independently selected from halogen, —CN, and—CF₃;

Embodiment 194 is the method of any one of embodiments 189-193, whereineach R^(2a) and R^(2b) is independently selected from F, Cl, —CN, and—CF₃;

Embodiment 195 is the method of any one of embodiments 189-194, whereinR^(2a) and R^(2b) are each F.

Embodiment 196 is the method of any one of embodiments 189-195, whereinA is —S(═O)₂—; A² is —C(═O)—; and A³ is —C(═O)—.

Embodiment 197 is the method of any one of embodiments 189-196, whereinB¹ and B² are each —NR^(3c)—.

Embodiment 198 is the method of embodiment 197 wherein R^(3c) ishydrogen or —CH₃.

Embodiment 199 is the method of embodiment 198, wherein R^(3c) ishydrogen.

Embodiment 200 is the method of any one of embodiments 189-199, whereinB³ is —NR^(3c)—.

Embodiment 201 is the method of embodiment 200, wherein R^(3c) ishydrogen.

Embodiment 202 is the method of any one of embodiments 189-201, whereinE is —NR^(9a)R^(9b)R^(9c+) or —S(═O)₂OR^(9a).

Embodiment 203 is the method of embodiment 202, wherein E is—NR^(9a)R^(9b)R^(9c+).

Embodiment 204 is the method of embodiment 203, wherein each R^(9a),R^(9b), and R^(9c) is hydrogen or —CH₃.

Embodiment 205 is the method of embodiment 204, wherein each R^(9a),R^(9b), and R^(9c) is hydrogen.

Embodiment 206 is the method of embodiment 204, wherein each R^(9a),R^(9b), and R^(9c) is —CH₃.

Embodiment 207 is the method of embodiment 202, wherein E is—S(═O)₂OR^(9a).

Embodiment 208 is the method of embodiment 207, wherein R^(9a) ishydrogen or —CH₃.

Embodiment 209 is the method of embodiment 208, wherein each R^(9a) ishydrogen.

Embodiment 210 is the method of embodiment 208, wherein each R^(9a) is—CH₃.

Embodiment 211 is the method of any one of embodiments 189-210, whereineach R^(6c) and R^(6d) is independently selected from hydrogen and —CH₃.

Embodiment 212 is the method of any one of embodiments 189-211, whereineach R^(3a) and R^(3b) is —CH₃.

Embodiment 213 is the method of any one of embodiments 189-212, whereinR^(11a) is hydrogen or —CH₃.

Embodiment 214 is the method of embodiment 213, wherein R^(11a) is —CH₃.

Embodiment 215 is the method of any one of embodiments 189-214, whereinR^(12a) is hydrogen or —CH₃.

Embodiment 216 is the method of embodiment 215, wherein R^(12a) is —CH₃.

Embodiment 217 is the method of any one of embodiments 189-216, whereineach R^(11b), R^(11c), R^(12b), and R^(12c) is hydrogen.

Embodiment 218 is a charged or zwitterion copolymer modifiedbiofouling-resistant device prepared by the method comprising:

-   -   a) contacting a surface of a silicon-based device with a        solution or suspension comprising a charged or zwitterion        copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the        silicon-based device, thereby generating the charged or        zwitterion copolymer modified device;        wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer.

Embodiment 219 is a charged or zwitterion copolymer modifiedbiofouling-resistant device prepared by the method comprising:

-   -   a) contacting a surface of a device with a solution or        suspension comprising a charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a light        source for a time sufficient to undergo photografting of the        charged or zwitterion copolymer onto the surface of the device,        thereby generating the charged or zwitterion copolymer modified        device;        wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and    -   wherein the charged or zwitterion copolymer having a        number-average molecular weight of between about 10,000 and        about 250,000.

Embodiment 220 is the device of embodiment 218 or 219, wherein the timesufficient to undergo photografting is at least 1 minute, at least 2minutes, 3 minutes, 4 minutes, 5 minutes, 6 minutes, 7 minutes, 8minutes, 9 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes or 30minutes.

Embodiment 221 is the device of any one of embodiments 218-220, whereinthe light source is an ultraviolet light source.

Embodiment 222 is the device of embodiment 221, wherein the ultravioletlight source has an intensity of at least 900 μW/cm².

Embodiment 223 is the device of embodiment 221 or 222, wherein theultraviolet light source has a wavelength of between 240 nm and 280 nm,between 240 nm and 275 nm, between 240 nm and 270 nm, between 240 nm and265 nm, between 240 nm and 260 nm, between 240 nm and 255 nm, between240 nm and 250 nm, between 240 nm and 245 nm, between 250 nm and 280 nm,between 250 nm and 275 nm, between 250 nm and 270 nm, between 250 nm and265 nm, between 250 nm and 260 nm, between 255 nm and 280 nm, between255 nm and 275 nm, between 255 nm and 270 nm, between 255 nm and 265 nm,between 255 nm and 260 nm, between 260 nm and 280 nm, between 260 nm and275 nm, between 260 nm and 270 nm, or between 270 nm and 280 nm.

Embodiment 224 is the device of embodiment 221 or 222, wherein theultraviolet light source has a wavelength of at least 240 nm, 245 nm,250 nm, 251 nm, 252 nm, 253 nm, 254 nm, 255 nm, 256 nm, 257 nm, 258 nm,259 nm, 260 nm, 261 nm, 262 nm, 263 nm, 264 nm, 265 nm, 266 nm, 267 nm,268 nm, 269 nm, 270 nm, 275 nm or 280 nm.

Embodiment 225 is the device of any one of embodiments 218-224, whereinthe solution or suspension of step a) is an aqueous solution orsuspension.

Embodiment 226 is the device of any one of embodiments 218-225, whereinphotografting of step b) is not affected by the presence of oxygen.

Embodiment 227 is the device of any one of embodiments 218-226, whereinthe charged or zwitterion compound comprises a compound of any one ofembodiments 1-75 or a copolymer of any one of embodiments 76-95.

Embodiment 228 is the device of any one of the embodiments 218-227,wherein the solution or suspension comprising a charged or zwitterioncompound has a concentration of the charged or zwitterion compound inthe solution or suspension between 1 mg/mL and 30 mg/mL.

Embodiment 229 is the device of embodiment 228, wherein theconcentration of the charged or zwitterion compound in the solution orsuspension is between 1 mg/mL and 25 mg/mL, between 1 mg/mL and 20mg/mL, between 1 mg/mL and 15 mg/mL, between 1 mg/mL and 10 mg/mL,between 1 mg/mL and 5 mg/mL, between 5 mg/mL and 30 mg/mL, between 5mg/mL and 25 mg/mL, between 5 mg/mL and 20 mg/mL, between 5 mg/mL and 15mg/mL, between 5 mg/mL and 10 mg/mL, between 10 mg/mL and 30 mg/mL,between 10 mg/mL and 25 mg/mL, between 10 mg/mL and 20 mg/mL, between 10mg/mL and 15 mg/mL, between 15 mg/mL and 30 mg/mL, between 15 mg/mL and25 mg/mL, between 15 mg/mL and 20 mg/mL, between 20 mg/mL and 30 mg/mL,or between 20 mg/mL and 25 mg/mL.

Embodiment 230 is the device of embodiment 228, wherein theconcentration of the charged or zwitterion compound in the solution orsuspension is about 1 mg/mL, 2 mg/mL, 3 mg/mL, 4 mg/mL, 5 mg/mL, 6mg/mL, 7 mg/mL, 8 mg/mL, 9 mg/mL, 10 mg/mL, 11 mg/mL, 12 mg/mL, 13mg/mL, 14 mg/mL, 15 mg/mL, 16 mg/mL, 17 mg/mL, 18 mg/mL, 19 mg/mL, 20mg/mL, 21 mg/mL, 22 mg/mL, 23 mg/mL, 24 mg/mL, 25 mg/mL, 26 mg/mL, 27mg/mL, 28 mg/mL, 29 mg/mL, or 30 mg/mL.

Embodiment 231 is the device of any one of embodiments 218-230, whereinthe concentration of the charged or zwitterion compound is between 0.1to 1 mg per square centimeter of the device.

Embodiment 232 is the device of embodiment 218, wherein the charged orzwitterion copolymer has a number-average molecular weight of betweenabout 10,000 and about 250,000

Embodiment 233 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 10,000 and about 20,000.

Embodiment 234 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 10,000 and about 40,000.

Embodiment 235 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 20,000 and about 60,000.

Embodiment 236 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 40,000 and about 100,000.

Embodiment 237 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 80,000 and about 160,000.

Embodiment 238 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 120,000 and about 200,000.

Embodiment 239 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 14,000 and about 21,000.

Embodiment 240 is the device of any one of embodiments 219-232, whereinthe charged or zwitterion copolymer has a number-average molecularweight of between about 15,000 and about 18,000.

Embodiment 241 is the device of embodiment 219, wherein the devicecomprises a carbon-based device or a silicon-based device containing amoiety capable of binding with the phenyl azide-zwitterion compound ofany one of embodiments 24-75 or a copolymer of any one of embodiments76-95.

Embodiment 242 is the device of embodiment 241, wherein the devicecomprises a silicon-based device.

Embodiment 243 is the device of embodiment 218 or 242, wherein thesilicon-based device comprises a polymer moiety.

Embodiment 244 is the device of embodiment 243, wherein thesilicon-based device comprises a siloxane polymer moiety, asesquisiloxane polymer moiety optionally having a ladder structure, asiloxane-silarylene polymer moiety, a silalkylene polymer moiety, apolysilane moiety, a polysilylene moiety, or a polysilazane moiety.

Embodiment 245 is the device of embodiment 244, wherein thesilicon-based device comprises a siloxane polymer moiety.

Embodiment 246 is the device of embodiment 241, wherein the devicecomprises a carbon-based device.

Embodiment 247 is the device of embodiment 246, wherein the carbon-baseddevice comprises a carbon-based polymer.

Embodiment 248 is the device of embodiment 246, wherein the carbon-baseddevice comprises a polyolefin moiety.

Embodiment 249 is the device of embodiment 248, wherein the polyolefinmoiety comprises polyethylene moiety, polypropylene moiety, polyvinylchloride moiety, polyvinylidene fluoride moiety, polytetrafluoroethylenemoiety, polychlorotrifluoroethylene moiety, or polystyrene moiety.

Embodiment 250 is the device of embodiment 247, wherein the carbon-basedpolymer comprises polyamide moiety, polyurethane moiety,phenol-formaldehyde resin moiety, polycarbonate moiety, polychloroprenemoiety, polyacrylonitrile moiety, polyimide moiety, or polyester moiety.

Embodiment 251 is the device of embodiment 247, wherein the carbon-basedpolymer comprises nylon.

Embodiment 252 is the device of embodiment 247, wherein the carbon-basedpolymer comprises polyethylene terephthalate.

Embodiment 253 is the device of any one of embodiments 218-252, whereinthe device is resistant to fouling.

Embodiment 254 is the device of embodiment 253, wherein the deviceprevents and/or reduces biofouling.

Embodiment 255 is the device of embodiment 254, wherein biofoulingcomprises microfouling or macrofouling.

Embodiment 256 is the device of embodiment 255, wherein microfoulingcomprises biofilm and bacterial adhesion.

Embodiment 257 is the device of embodiment 255 or 256, whereinmicrofouling is formed by a bacterium or a fungus.

Embodiment 258 is the device of any one of embodiments 255-257, whereinmicrofouling is formed by a gram-positive bacterium.

Embodiment 259 is the device of embodiment 258, wherein thegram-positive bacterium comprises a bacterium from the genusActinomyces, Arthrobacter, Bacillus, Clostridium, Corynebacterium,Enterococcus, Lactococcus, Listeria, Micrococcus, Mycobacterium,Staphylococcus, or Streptococcus.

Embodiment 260 is the device of embodiment 258 or 259, wherein thegram-positive bacterium comprises Actinomyces spp., Arthrobacter spp.,Bacillus licheniformis, Clostridium difficile, Clostridium spp.,Corynebacterium spp., Enterococcus faecalis, Lactococcus spp., Listeriamonocytogenes, Micrococcus spp., Mycobacterium spp., Staphylococcusaureus, Staphylococcus epidermidis, Streptococcus pneumoniae, orStreptococcus pyogenes.

Embodiment 261 is the device of any one of embodiments 255-257, whereinmicrofouling is formed by a gram-negative bacterium.

Embodiment 262 is the device of embodiment 261, wherein thegram-negative bacterium comprises a bacterium from the genusAlteromonas, Aeromonas, Desulfovibrio, Escherichia, Fusobacterium,Geobacter, Haemophilus, Klebsiella, Legionella, Porphyromonas, Proteus,Pseudomonas, Serratia, Shigella, Salmonella, or Vibrio.

Embodiment 263 is the device of embodiment 261 or 262, wherein thegram-negative bacterium comprises Alteromonas spp., Aeromonas spp.,Desulfovibrio spp., Escherichia coli, Fusobacterium nucleatum, Geobacterspp., Haemophilus spp., Klebsiella spp., Legionella pneumophila,Porphyromonas spp., Pseudomonas aeruginosa, Proteus vulgaris, Proteusmirabilis, Proteus penneri, Serratia spp., Shigella dysenteriae,Shigella flexneri, Shigella boydii, Shigella sonnei, Salmonella bongori,Salmonella enterica, or Vibrio Cholerae.

Embodiment 264 is the device of embodiment 257, wherein the bacterium isa marine bacterium.

Embodiment 265 is the device of embodiment 264, wherein the marinebacterium comprises Pseudoalteromonas spp. or Shewanella spp.

Embodiment 266 is the device of any one of embodiments 255-257, whereinmicrofouling is formed by a fungus.

Embodiment 267 is the device of embodiment 266, wherein the funguscomprises Candida albicans, Candida glabrata, Candida rugose, Candidaparapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconisresinae.

Embodiment 268 is the device of embodiment 255, wherein macrofoulingcomprises calcareous fouling organism or non-calcareous foulingorganism.

Embodiment 269 is the device of embodiment 268, wherein calcareousfouling organism comprises barnacle, bryozoan, mollusk, polychaete, tubeworm, or zebra mussel.

Embodiment 270 is the device of embodiment 268, wherein non-calcareousfouling organism comprises seaweed, hydroids, or algae.

Embodiment 271 is the device of any one of embodiments 218-270, whereinthe formation of biofouling on a surface of a device is reduced by about10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%, 99.9%, ormore relative to unmodified surface of a device.

Embodiment 272 is the device of any one of embodiments 218-271, whereinthe device is further coated with an additional agent.

Embodiment 273 is the device of embodiment 272, wherein the additionalagent is an antimicrobial agent.

Embodiment 274 is the device of embodiment 272, wherein the additionalagent is a chemical disinfectant.

Embodiment I is a copolymer comprising:

-   -   a) a repeating unit of Formula (VII):

-   -   wherein    -   each R^(1a) and R^(1b) is independently selected from hydrogen        and halogen;    -   each R^(2a) and R^(2b) is independently selected from halogen,        —CN, and optionally substituted C₁-C₆ fluoroalkyl;    -   each A¹ and A² is independently selected from —C(═O)—, —S(═O)—,        —S(═O)₂—, and —S(═O)(═NR^(3c))—;    -   each B¹ and B² is independently selected from —O— and —NR^(3c)—;        Z¹ is —(CR^(6c)R^(6d))_(s)—;    -   each R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d) is        independently selected from hydrogen, halogen, —CN, —OR^(9a),        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₄        fluoroalkyl, optionally substituted C₂-C₆ alkenyl,        —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and        —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(11a), R^(11b), and R^(11c) is independently        selected from hydrogen, optionally substituted C₁-C₄ alkyl, and        optionally substituted aryl;    -   n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and    -   s is an integer selected from 1, 2, 3, 4, and 5;    -   b) a repeating unit of Formula (VIII):

-   -   wherein,    -   A³ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;    -   B³ is —O— or —NR^(3c)—;    -   D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a);    -   Z² is —(CR^(6c)R^(6d))_(t)—;    -   Z³ is —(CR^(6c)R^(6d))_(p);    -   each R^(3a) and R^(3b) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, and optionally substituted        benzyl;    -   each R^(6c) and R^(6d) is independently selected from hydrogen,        halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,        optionally substituted C₁-C₄ fluoroalkyl, optionally substituted        C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a),        —C(═O)O⁻, and —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(12a), R^(12b), and R^(12c) is independently        selected from hydrogen, optionally substituted C₁-C₄ alkyl, and        optionally substituted aryl;    -   t is an integer selected from 1, 2, 3, 4, or 5;    -   p is an integer selected from 1, 2, 3, 4, or 5; and    -   wherein the repeating unit of Formula (VIII) is charged or        zwitterionic; and    -   c) a repeating unit of Formula (IX):

-   -   A⁴ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—;    -   B⁴ is —O— or —NR^(3c)—;    -   Z⁴ is —(CR^(6c)R^(6d))_(k)—;    -   E is —CN, —OR^(9a), —NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+)        optionally substituted C₁-C₄ alkyl, optionally substituted C₁-C₆        fluoroalkyl, —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or        —C(═O)OR^(9a);    -   each R^(6c), and R^(6d) is independently selected from hydrogen,        halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl,        optionally substituted C₁-C₄ fluoroalkyl, optionally substituted        C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a),        —C(═O)O⁻, and —C(═O)OR^(9a);    -   each R^(3c) and R^(3d) is independently selected from hydrogen,        optionally substituted C₁-C₄ alkyl, —X-optionally substituted        C₁-C₄ alkyl, optionally substituted C₂-C₆ alkenyl, and        optionally substituted aryl;    -   X is —C(═O)—, —S(═O)—, or —S(═O)₂—;    -   each R^(9a), R^(9b), R^(9c), R^(13a), R^(13b), and R^(13c) is        independently selected from hydrogen, optionally substituted        C₁-C₄ alkyl, and optionally substituted aryl; and    -   k is an integer selected from 1, 2, 3, 4, or 5.

Embodiment II is the copolymer of embodiment I, wherein each R^(1a),R^(1b), R^(2a), and R^(2b) is F.

Embodiment III is the copolymer of embodiment I or II, wherein A¹ is—S(═O)₂— and each A², A³, and A⁴ is —C(═O)—.

Embodiment IV is the copolymer of any one of embodiments I-III, whereineach B¹, B², and B³ is independently —O— or —NR^(3c)—.

Embodiment V is the copolymer of any one of embodiments I-IV, whereineach R^(3c) is hydrogen or —CH₃.

Embodiment VI is the copolymer of any one of embodiments I-V, wherein Dis —S(═O)₂O— or —C(═O)O⁻.

Embodiment VII is the copolymer of any one of embodiments I-VI, whereinE is —NR^(9a)R^(9b)R^(9c+) or —S(═O)₂OR^(9a).

Embodiment VIII is the copolymer of any one of embodiments I-VII,wherein each R^(9a), R^(9b), and R^(9c) is independently hydrogen orC₁-C₄ alkyl.

Embodiment IX is the copolymer of any one of embodiments I-VIII, whereineach R^(3a) and R^(3b) is —CH₃.

Embodiment X is the copolymer of any one of embodiments I-IX, whereineach R^(3c), R^(3d), R^(4c), R^(4d), R^(5d), R^(5e), R^(6c), and R^(6d)is hydrogen.

Embodiment XI is the copolymer of any one of embodiments I-X, whereineach R^(11a), R^(12a), and R^(13a) is hydrogen or —CH₃.

Embodiment XII is the copolymer of any one of embodiments I-XI, whereineach R^(11b), R^(11c), R^(12b), R^(12c), R^(13b), and R^(13c) ishydrogen.

Embodiment XIII is the copolymer of any one of embodiments I-XII,wherein n is 0, 1, or 2.

Embodiment XIV is the copolymer of any one of embodiments I-XIII,wherein each s, t, p, and k is independently 1, 2 or 3.

Embodiment XV is a medical device coated with a compound of any one ofembodiments I-XIV.

Embodiment XVI is a biofouling-resistant medical device, wherein asurface of the medical device is coated with a compound of any one ofembodiments I-XIV.

Embodiment XVII is the biofouling-resistant medical device of embodimentXVI, wherein the medical device comprises an implant, an IV, aprosthesis, suturing material, valve, stent, catheter, rod, shunt,scope, a contact lens, tubing, wiring, electrode, clip, fastener,syringe, container, or a combination thereof.

Embodiment XVIII is the biofouling-resistant medical device ofembodiment XVI or XVII, wherein the medical device is a catheter.

Embodiment XIX is the biofouling-resistant medical device of any one ofembodiments XVI-XVIII, wherein the biofouling is produced by abacterium, a virus, and/or a fungus.

Embodiment XX is a method of making a biofouling-resistant medicaldevice, comprising:

-   -   a) contacting a surface of a device with a mixture comprising a        charged or zwitterion copolymer; and    -   b) treating the surface of the device of step a) with a heat        source for a time sufficient to undergo thermografting of the        copolymer onto the surface of the device, thereby making the        biofouling-resistant device;    -   wherein the charged or zwitterion copolymer comprises a phenyl        azide-based copolymer; and wherein the charged or zwitterion        copolymer having a number-average molecular weight of between        about 10,000 and about 250,000.

Embodiment XXI is the method of any one of embodiments XX, wherein thetime sufficient to undergo thermografting is 1 minute, 2 minutes, 3minutes, 4 minutes, 5 minutes, 6 minutes, 7 minutes, 8 minutes, 9minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 45minutes, 1 hour, 1.5 hours, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours,9 hours, 12 hours, 18 hours, or 24 hours.

Embodiment XXII is the method of embodiment XX or XXI, wherein the heatsource provides a grafting temperature between 60° C. and 80° C.,between 80° C. and 100° C., between 100° C. and 120° C., between 120° C.and 140° C., between 140° C. and 160° C., between 160° C. and 180° C.,between 180° C. and 200° C., between 200° C. and 220° C., or between220° C. and 240° C.

Embodiment XXIII is the method of any one of embodiments XX-XXII,wherein the solution or suspension of step a) is an aqueous solution orsuspension.

Embodiment XXIV is the method of any one of embodiments XX-XXIII,wherein thermografting of step b) is not affected by the presence ofoxygen.

Embodiment XXV is the method of any one of embodiments XX-XXIV, whereinthe charged or zwitterion copolymer is a copolymer of any one ofembodiments 1-14.

Embodiment XXVI is the method of any one of embodiments XX-XXV, whereinthe solution or suspension comprising a charged or zwitterion copolymerhas a concentration of the charged or zwitterion copolymer in thesolution or suspension between 1 mg/mL and 30 mg/mL.

Embodiment XXVII is the method of any one of embodiments XX-XXV, whereinthe concentration of the charged or zwitterion copolymer in the solutionor suspension is between 1 mg/mL and 25 mg/mL, between 1 mg/mL and 20mg/mL, between 1 mg/mL and 15 mg/mL, between 1 mg/mL and 10 mg/mL,between 1 mg/mL and 5 mg/mL, between 5 mg/mL and 30 mg/mL, between 5mg/mL and 25 mg/mL, between 5 mg/mL and 20 mg/mL, between 5 mg/mL and 15mg/mL, between 5 mg/mL and 10 mg/mL, between 10 mg/mL and 30 mg/mL,between 10 mg/mL and 25 mg/mL, between 10 mg/mL and 20 mg/mL, between 10mg/mL and 15 mg/mL, between 15 mg/mL and 30 mg/mL, between 15 mg/mL and25 mg/mL, between 15 mg/mL and 20 mg/mL, between 20 mg/mL and 30 mg/mL,or between 20 mg/mL and 25 mg/mL.

Embodiment XXVIII is the method of any one of embodiments XX-XXVII,wherein the device comprises a carbon-based device or a silicon-baseddevice.

Embodiment XXIX is the method of any one of embodiments XX-XXVIII,wherein the device comprises a silicon-based device, wherein thesilicon-based device comprises a silicon-based polymer moiety.

Embodiment XXX is the method of any one of embodiments XX-XXIX, whereinthe biofouling is produced by a bacterium, a virus, and/or a fungus.

1. A copolymer comprising: a) a repeating unit of Formula (VII):

wherein each R^(1a) and R^(1b) is independently selected from hydrogenand halogen; each R^(2a) and R^(2b) is independently selected fromhalogen, —CN, and optionally substituted C₁-C₆ fluoroalkyl; each A¹ andA² is independently selected from —C(═O)—, —S(═O)—, —S(═O)₂—, and—S(═O)(═NR^(3c))—; each B¹ and B² is independently selected from —O— and—NR^(3c); Z¹ is —(CR^(6c)R^(6d))_(s)—; each R^(4c), R^(4d), R^(5d),R^(5e), R^(6c), and R^(6d) is independently selected from hydrogen,halogen, —CN, —OR^(9a), optionally substituted C₁-C₄ alkyl, optionallysubstituted C₁-C₄ fluoroalkyl, optionally substituted C₂-C₆ alkenyl,—NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and —C(═O)OR^(9a);each R^(3c) and R^(3d) is independently selected from hydrogen,optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄alkyl, optionally substituted C₂-C₆ alkenyl, and optionally substitutedaryl; X is —C(═O)—, —S(═O)—, or —S(═O)₂—; each R^(9a), R^(11a), R^(11b)and R^(11c) is independently selected from hydrogen, optionallysubstituted C₁-C₄ alkyl, and optionally substituted aryl; n is aninteger selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and s is an integerselected from 1, 2, 3, 4, and 5; b) a repeating unit of Formula (VIII):

wherein, A³ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—; B³ is—O— or —NR^(3c)—; D is —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, or—C(═O)OR^(9a); Z² is —(CR^(6c)R^(6d))_(t)—; Z³ is —(CR^(6c)R^(6d))_(p)—;each R^(3a) and R^(3b) is independently selected from hydrogen,optionally substituted C₁-C₄ alkyl, and optionally substituted benzyl;each R^(6C) and R^(6d) is independently selected from hydrogen, halogen,—CN, —OR^(9a), optionally substituted C₁-C₄ alkyl, optionallysubstituted C₁-C₄ fluoroalkyl, optionally substituted C₂-C₆ alkenyl,—NR^(3c)R^(3d), —S(═O)₂O⁻, —S(═O)₂OR^(9a), —C(═O)O⁻, and —C(═O)OR^(9a);each R^(3c) and R^(3d) is independently selected from hydrogen,optionally substituted C₁-C₄ alkyl, —X-optionally substituted C₁-C₄alkyl, optionally substituted C₂-C₆ alkenyl, and optionally substitutedaryl; X is —C(═O)—, —S(═O)—, or —S(═O)₂—; each R^(9a), R^(12a), R^(12b)and R^(12c) is independently selected from hydrogen, optionallysubstituted C₁-C₄ alkyl, and optionally substituted aryl; t is aninteger selected from 1, 2, 3, 4, or 5; p is an integer selected from 1,2, 3, 4, or 5; and wherein the repeating unit of Formula (VIII) ischarged or zwitterionic; and c) a repeating unit of Formula (IX):

A⁴ is —C(═O)—, —S(═O)—, —S(═O)₂—, or —S(═O)(═NR^(3c))—; B⁴ is —O— or—NR^(3c)—; Z⁴ is —(CR^(6c)R^(6d))_(k)—; E is —CN, —OR^(9a),—NR^(9a)R^(9b), —NR^(9a)R^(9b)R^(9c+) optionally substituted C₁-C₄alkyl, optionally substituted C₁-C₆ fluoroalkyl, —S(═O)₂O⁻,—S(═O)₂OR^(9a), —C(═O)O⁻, or —C(═O)OR^(9a); each R^(6c), and R^(6d) isindependently selected from hydrogen, halogen, —CN, —OR^(9a), optionallysubstituted C₁-C₄ alkyl, optionally substituted C₁-C₄ fluoroalkyl,optionally substituted C₂-C₆ alkenyl, —NR^(3c)R^(3d), —S(═O)₂O⁻,—S(═O)₂OR^(9a), —C(═O)O⁻, and —C(═O)OR^(9a); each R^(3c) and R^(3d) isindependently selected from hydrogen, optionally substituted C₁-C₄alkyl, —X-optionally substituted C₁-C₄ alkyl, optionally substitutedC₂-C₆ alkenyl, and optionally substituted aryl; X is —C(═O)—, —S(═O)—,or —S(═O)₂—; each R^(9a), R^(9b), R^(9c), R^(13a), R^(13b), and R^(13c)is independently selected from hydrogen, optionally substituted C₁-C₄alkyl, and optionally substituted aryl; and k is an integer selectedfrom 1, 2, 3, 4, or
 5. 2. The copolymer of claim 1, wherein each R^(1a),R^(1b), R^(2a), and R^(2b) is F.
 3. The copolymer of claim 1, wherein Ais —S(═O)₂— and each A², A³, and A⁴ is —C(═O)—.
 4. The copolymer ofclaim 1, wherein each B¹, B², and B³ is independently —O— or —NR^(3c)—.5. The copolymer of claim 4, wherein each R^(3c) is hydrogen or —CH₃. 6.The copolymer of claim 1, wherein D is —S(═O)₂O⁻ or —C(═O)O⁻.
 7. Thecopolymer of claim 1, wherein E is —NR^(9a)R^(9b)R^(9c+) or—S(═O)₂OR^(9a).
 8. The copolymer of claim 7, wherein each R^(9a),R^(9b), and R^(9c) is independently hydrogen or C₁-C₄ alkyl.
 9. Thecopolymer of claim 1, wherein each R^(3a) and R^(3b) is —CH₃.
 10. Thecopolymer of claim 1, wherein each R^(3c), R^(3d), R^(4c), R^(4d),R^(5d), R^(5e), R^(6c), and R^(6d) is hydrogen.
 11. The copolymer ofclaim 1, wherein each R^(11a), R^(12a), and R^(13a) is hydrogen or —CH₃.12. The copolymer of claim 1, wherein each R^(11b), R^(11c), R^(12b),R^(12c), R^(13b), and R^(13c) is hydrogen.
 13. The copolymer of claim 1,wherein n is 0, 1, or
 2. 14. The copolymer of claim 1, wherein each s,t, p, and k is independently 1, 2 or
 3. 15. A medical device coated witha compound of claim
 1. 16. A biofouling-resistant medical device,wherein a surface of the medical device is coated with a compound ofclaim
 1. 17. The biofouling-resistant medical device of claim 16,wherein the medical device comprises an implant, an IV, a prosthesis,suturing material, valve, stent, catheter, rod, shunt, scope, a contactlens, tubing, wiring, electrode, clip, fastener, syringe, container, ora combination thereof.
 18. The biofouling-resistant medical device ofclaim 17, wherein the medical device is a catheter.
 19. Thebiofouling-resistant medical device of claim 16, wherein the biofoulingis produced by a bacterium, a virus, and/or a fungus.
 20. A method ofmaking a biofouling-resistant medical device, comprising: a) contactinga surface of a device with a mixture comprising a charged or zwitterioncopolymer; and b) treating the surface of the device of step a) with aheat source for a time sufficient to undergo thermografting of thecopolymer onto the surface of the device, thereby making thebiofouling-resistant device; wherein the charged or zwitterion copolymercomprises a phenyl azide-based copolymer; and wherein the charged orzwitterion copolymer having a number-average molecular weight of betweenabout 10,000 and about 250,000. 21.-30. (canceled)